Name: 150-86-7|(7R,11R,E)-3,7,11,15-Tetramethylhexadec-2-en-1-ol|95%
Brand: Ambeed
SKU: A178143
Price: 9.0 USD
Availability: InStock
Rating: 96 (28 reviews)

1
[ 481-85-6 ]
[ 150-86-7 ]
[ 84-80-0 ]

Yield	Reaction Conditions	Operation in experiment
	With boron trifluoride anschliessend Behandeln mit Ag₂O;

Reference： [1]Hirschmann; Miller; Wendler [Journal of the American Chemical Society, 1954, vol. 76, p. 4592] Isler; Doebel [Helvetica Chimica Acta, 1954, vol. 37, p. 225,229]

2
[ 481-85-6 ]
[ 150-86-7 ]
[ 74610-11-0 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,4-dioxane; oxalic acid Siedetemperatur;
	With oxalic acid at 140℃;

Reference： [1]Fieser [Journal of Biological Chemistry, 1940, vol. 133, p. 391,395] Fieser [Journal of the American Chemical Society, 1939, vol. 61, p. 3467,3473] Tishler; Fieser; Wendler [Journal of the American Chemical Society, 1940, vol. 62, p. 1982,1990] Wagner,A. F.; Folkers,K. [Vitamins and Coenzymes <New York 1964> S. 419] Fieser et al. [Journal of the American Chemical Society, 1939, vol. 61, p. 2559]
[2]Fieser [Journal of Biological Chemistry, 1940, vol. 133, p. 391,395] Fieser [Journal of the American Chemical Society, 1939, vol. 61, p. 3467,3473] Tishler; Fieser; Wendler [Journal of the American Chemical Society, 1940, vol. 62, p. 1982,1990] Wagner,A. F.; Folkers,K. [Vitamins and Coenzymes <New York 1964> S. 419] Fieser et al. [Journal of the American Chemical Society, 1939, vol. 61, p. 2559]

3
[ 481-85-6 ]
[ 150-86-7 ]
[ 572-96-3 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,4-dioxane; oxalic acid at 75℃;
	With acetic acid; samarium(III) trifluoromethanesulfonate In Petroleum ether for 4h; Inert atmosphere;	1.2 under the protection of nitrogen in the above solution added2 g of samarium trifluoromethanesulfonate2g acetic acid, stirring heated to reflux, slowly dropping containing 60g 50% of the phytol in petroleum ether solution,After the dropwise addition, the mixture was kept at reflux for 4 hours,After completion of the reaction,After cooling to room temperature, 50 g of ferric chloride was added,The reaction was stirred for 5 hours,After the filtrate was washed with saturated brine, 4g of anhydrous sodium sulfate, 3g of aluminum oxide and 3g of activated carbon were added to decolorize and filter.The filtrate was concentrated under reduced pressure to give vitamin K126.5g.

Reference： [1]Current Patent Assignee: MERCK & CO INC - US2307084, 1940, A Fieser [Journal of the American Chemical Society, 1939, vol. 61, p. 2559,3467, 3471] Tishler; Fieser; Wendler [Journal of the American Chemical Society, 1940, vol. 62, p. 1982,1990]
[2]Current Patent Assignee: SHANDONG GUANGTONGBAO PHARMACEUTICALS - CN105399615, 2016, A Location in patent: Paragraph 0023; 0024; 0026

4
[ 700-13-0 ]
[ 150-86-7 ]
[ 74515-24-5 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,4-dioxane; oxalic acid at 75℃;

Reference： [1]Fieser; Tishler; Wendler [Journal of the American Chemical Society, 1940, vol. 62, p. 2861,2865]

5
[ 700-13-0 ]
[ 150-86-7 ]
[ 186537-56-4 ]

Yield	Reaction Conditions	Operation in experiment
77%	With scandium tris(trifluoromethanesulfonate) In toluene at 110℃; for 0.5h; Microwave irradiation; Green chemistry;
	With hydrogenchloride; diethyl ether
	With ethanol; phosphorus pentoxide

	With zinc(II) chloride; decalin
	With boron trifluoride 1.) n-heptane, 90 deg C, 5 min, 2.) reflux, 18 h; Multistep reaction;
	With hydrogenchloride; diethyl ether
	With zinc(II) chloride; decalin

Reference： [1]Rotolo; Calcio Gaudino; Carnaroglio; Barge; Tagliapietra; Cravotto [RSC Advances, 2016, vol. 6, # 68, p. 63515 - 63518]
[2]Current Patent Assignee: ROCHE HOLDING AG - DE731972, 1938, C [DRP/DRBP Org.Chem.][DRP/DRBP Org.Chem.]
[3]Current Patent Assignee: MERCK & CO INC - US2230659, 1939, A
[4]Weichet; Hodrova [Collection of Czechoslovak Chemical Communications, 1957, vol. 22, p. 595,597] Bergel et al. [Journal of the Chemical Society, 1938, p. 1375,1380] Current Patent Assignee: ROCHE HOLDING AG - DE731972, 1938, C [DRP/DRBP Org.Chem.][DRP/DRBP Org.Chem.] Smith et al. [Journal of the American Chemical Society, 1939, vol. 61, p. 2617]
[5]Brownstein; Burton; Hughes; Ingold [Journal of Organic Chemistry, 1989, vol. 54, # 3, p. 560 - 569]
[6]Current Patent Assignee: ROCHE HOLDING AG - US2411967, 1938, A
[7]Current Patent Assignee: ROCHE HOLDING AG - US2411967, 1938, A

6
[ 5307-05-1 ]
[ 150-86-7 ]
[ 121600-35-9 ]

Reference： [1]Journal of the Chemical Society,1959,p. 3362,3369

7
[ 5307-05-1 ]
[ 150-86-7 ]
[ 91-86-1 ]

Reference： [1]Journal of the Chemical Society,1959,p. 3362,3369

8
[ 5307-05-1 ]
[ 150-86-7 ]
[ 91-86-1 ]
[ 119-13-1 ]

Reference： [1]Journal of the Chemical Society,1959,p. 3362,3369

9
[ 14786-82-4 ]
[ 150-86-7 ]
[ 148-57-2 ]

Reference： [1]Journal of the Chemical Society,1959,p. 3350,3356

10
[ 5344-97-8 ]
[ 150-86-7 ]
[ 15035-98-0 ]

Reference： [1]Patent: US358287,1941,
[2]Patent: DE707956,1939,
DRP/DRBP Org.Chem.,

11
[ 5690-26-6 ]
[ 150-86-7 ]
[ 107421-74-9 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,4-dioxane; oxalic acid at 91℃; bei Lichtausschluss; Isolierung ueber 2-<(<i>R</i>:11<i>R</i>)-<i>trans</i>-phytyl>-naphthalintriol-(1.3.4) <nicht naher beschrieben>;

Reference： [1]Fieser; Gates [Journal of the American Chemical Society, 1941, vol. 63, p. 2948,2952]

12
[ 38262-43-0 ]
[ 150-86-7 ]
(2Ξ:3Ξ)-2.3-dimethyl-2-((7R:11R)-trans-phytyl)-2.3-dihydro-naphthoquinone-(1.4) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1,4-dioxane; oxalic acid at 75℃;

Reference： [1]Tishler; Fieser; Wendler [Journal of the American Chemical Society, 1940, vol. 62, p. 1982,1990]

13
[ 3096-71-7 ]
[ 150-86-7 ]
(2RS)-2,5,8-Trimethyl-6-(-4-nitro-benzoylamino)-2-((4R,8R)-4,8,12-trimethyl-tridecyl)-chroman [ No CAS ]

Reference： [1]Patent: DE706795,1939,
DRP/DRBP Org.Chem.,
[2]Patent: US2358287,1941,

14
[ 99075-42-0 ]
[ 150-86-7 ]
(2RS)-6-Amino-2,5,7,8-tetramethyl-2-((4R,8R)-4,8,12-trimethyl-tridecyl)-chroman [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With formic acid Erwaermen des Reaktionsprodukts mit wss.-aethanol. Salzsaeure;
	With formic acid Erwaermen des Reaktionsprodukts mit wss.-aethanol. Salzsaeure;

Reference： [1]Smith; Renfrow; Opie [Journal of the American Chemical Society, 1942, vol. 64, p. 1082]
[2]Current Patent Assignee: MERCK & CO INC - US2358287, 1941, A Current Patent Assignee: MERCK & CO INC - US2358286, 1939, A Current Patent Assignee: MERCK KGAA - DE703957, 1941, C [DRP/DRBP Org.Chem.][DRP/DRBP Org.Chem.]

15
[ 92892-04-1 ]
[ 150-86-7 ]
(2RS)-6-Amino-2,5,7,8-tetramethyl-2-((4R,8R)-4,8,12-trimethyl-tridecyl)-chroman [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With formic acid Hydrieren des Reaktionsprodukts an Palladium/Kohle in wss.-aethanol. Salzsaeure;
	With formic acid Hydrieren des Reaktionsprodukts an Palladium/Kohle in wss.-aethanol. Salzsaeure;

Reference： [1]Current Patent Assignee: MERCK KGAA - DE741688, 1940, C [DRP/DRBP Org.Chem.][DRP/DRBP Org.Chem.]
[2]Current Patent Assignee: MERCK & CO INC - US2343773, 1941, A

16
[ 150-86-7 ]
[ 16825-16-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With ozone In methanol; dichloromethane at -20℃; for 6.5h;	14 Example 14, Preparation of Compound XVIII Put 50.0g (0.17mol) of phytol XVII in a dry reaction flask, add 500mL of dichloromethane and 100mL of methanol solution, pump ozone gas into the mixed solution, react at -20°C for 6.5h, remove under reduced pressure The organic solvent was subjected to column chromatography to obtain 38.5 g of a colorless oily liquid with a yield of 85%.
76%	Stage #1: [R-[R,R-(E)]]-3,7,11,15-tetramethyl-2-hexadecen-1-ol With ozone In methanol; dichloromethane at -78℃; Stage #2: With dimethylsulfane In methanol; dichloromethane at 20℃; for 2.5h; Further stages.;
75%	With potassium permanganate In acetone

72%	With potassium permanganate In acetone at 20℃; for 4h;
72%	With potassium permanganate In acetone for 3h;
70%	With potassium permanganate In acetone
	With ozone
	With ozone
	With formic acid; dihydrogen peroxide; ozone 1.) ethyl chloride, -78 deg C, 2.) RT, 4 h; Yield given. Multistep reaction;
	With ozone In methanol; dichloromethane at -78℃; for 1h;

Reference： [1]Current Patent Assignee: REFINER UNIV - CN114105932, 2022, A Location in patent: Paragraph 0075; 0144-0146
[2]Zhao, Liqin; Jin, Chunyang; Mao, Zisu; Gopinathan, Madathil B.; Rehder, Kenneth; Brinton, Roberta D. [Journal of Medicinal Chemistry, 2007, vol. 50, # 18, p. 4471 - 4481]
[3]Mizuguchi, Eisaku; Takemoto, Masumi; Achiwa, Kazuo [Tetrahedron Asymmetry, 1993, vol. 4, # 9, p. 1961 - 1964]
[4]Nam, Tae-Gyu; Rector, Christopher L.; Kim, Hye-Young; Sonnen, Andreas F.-P.; Meyer, Roland; Nau, Werner M.; Atkinson, Jeffrey; Rintoul, Julia; Pratt, Derek A.; Porter, Ned A. [Journal of the American Chemical Society, 2007, vol. 129, # 33, p. 10211 - 10219]
[5]Bieszczad, Bartosz; Gilheany, Declan G. [Organic and Biomolecular Chemistry, 2017, vol. 15, # 31, p. 6483 - 6492]
[6]Rontani [Tetrahedron Letters, 1991, vol. 32, # 45, p. 6551 - 6552]
[7]Burrell,J.W.K. et al. [Journal of the Chemical Society C: Organic, 1966, p. 2144 - 2154] McHale et al. [Journal of the Chemical Society, 1958, p. 1600,1603]
[8]Bessiere-Chretien,Y.; Marion,J.P. [Bulletin de la Societe Chimique de France, 1970, p. 3013 - 3019]
[9]Suga, Takayuki; Ohta, Shinji; Nakai, Akinori; Munesada, Kiyotaka [Journal of Organic Chemistry, 1989, vol. 54, # 14, p. 3390 - 3393]
[10]Wu, Zhongtao; Harutyunyan, Syuzanna R.; Minnaard, Adriaan J. [Chemistry - A European Journal, 2014, vol. 20, # 44, p. 14250 - 14255]

17
[ 571-60-8 ]
[ 144-62-7 ]
[ 150-86-7 ]
[ 34625-86-0 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,4-dioxane at 60 - 65℃; Behandeln des Reaktionsprodukts mit Ag₂O in Aether;

Reference： [1]Fieser; Tishler; Wendler [Journal of the American Chemical Society, 1940, vol. 62, p. 2861,2865]

18
[ 34987-32-1 ]
[ 144-62-7 ]
[ 150-86-7 ]
[ 106375-23-9 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,4-dioxane at 75℃; Behandeln des Reaktionsprodukts mit Ag₂O und MgSO₄ in Aether;

Reference： [1]Fieser [Journal of the American Chemical Society, 1939, vol. 61, p. 3467,3473]

19
[ 690228-98-9 ]
[ 144-62-7 ]
[ 150-86-7 ]
2.6-dimethyl-3-((7R:11R)-trans-phytyl)-naphthoquinone-(1.4) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1,4-dioxane at 75℃; Behandeln der Reaktionsprodukte mit Ag₂O und MgSO₄ in Aether;

Reference： [1]Fieser [Journal of the American Chemical Society, 1939, vol. 61, p. 2559,3467, 3474]

20
[ 690228-98-9 ]
[ 150-86-7 ]
[ 76-03-9 ]
2.6-dimethyl-3-((7R:11R)-trans-phytyl)-naphthoquinone-(1.4) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1,4-dioxane at 75℃; Behandeln der Reaktionsprodukte mit Ag₂O und MgSO₄ in Aether;

Reference： [1]Fieser [Journal of the American Chemical Society, 1939, vol. 61, p. 2559,3467, 3474]

21
[ 150-86-7 ]
[ 13754-69-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With manganese(IV) oxide In dichloromethane for 24h; Reflux;
75%	With pyridine; chromium(VI) oxide In dichloromethane
74%	With pyridinium chlorochromate In dichloromethane for 6h; Reflux;

74%	With pyridinium chlorochromate for 6h; Reflux;	PhY-12(3, 7, 11, 15-tetramethyl-2-hexadecenal) Pyridinium chlorochromate (3 mmol) was added to a solutionof phytol (2 mmol) in dry CH2 Cl2. The reaction mixturewas reflux for 6 h, and then the solvent was removed byevaporation. The residue was extracted with chloroform inexcess water. The combined organic extracts were dried andevaporated to give crude products which, after purificationby column chromatography on silica gel, afforded pureproduct 12 (PhY-12) as a viscous colorless liquid in 74%yield (435.5 mg) (purity >95%).
	With pyridine; chromium(VI) oxide; silica gel; acetic acid In dichloromethane
	With manganese(IV) oxide In dichloromethane
	With manganese(IV) oxide
	With manganese(IV) oxide In Petroleum ether Heating;
	With pyridine; chromium(VI) oxide In dichloromethane

Reference： [1]Guerrero, Angel; Ramos, Victoria Elena; López, Sergio; Alvarez, José María; Domínguez, Aroa; Coca-Abia, María Milagro; Bosch, María Pilar; Quero, Carmen [Journal of Agricultural and Food Chemistry, 2019, vol. 67, # 1, p. 72 - 80]
[2]Rontani [Tetrahedron Letters, 1991, vol. 32, # 45, p. 6551 - 6552]
[3]Upadhyay, Harish C.; Dwivedi, Gaurav R.; Roy, Sudeep; Sharma, Ashok; Darokar, Mahendra P.; Srivastava, Santosh K. [ChemMedChem, 2014, vol. 9, # 8, p. 1860 - 1868]
[4]Saxena, Archana; Upadhyay, Harish C.; Cheema, Harveer S.; Srivastava, Santosh K.; Darokar, Mahendra P.; Bawankule, Dnyaneshwar U. [Medicinal Chemistry Research, 2018, vol. 27, # 5, p. 1345 - 1354]
[5]Singh,R.P. et al. [Tetrahedron, 1979, vol. 35, p. 1789 - 1793]
[6]Burrell,J.W.K. et al. [Journal of the Chemical Society C: Organic, 1966, p. 2144 - 2154]
[7]Jackman; Rueegg; Ryser; von Planta; Gloor; Mayer; Schudel; Kofler; Isler [Helvetica chimica acta, 1965, vol. 48, # 6, p. 1332 - 1349] Bessiere-Chretien,Y.; Marion,J.P. [Bulletin de la Societe Chimique de France, 1970, p. 3013 - 3019]
[8]Spyckerelle,C. et al. [Tetrahedron, 1972, vol. 28, p. 5703 - 5713]
[9]Belt, Simon T.; Rontani, Jean-François; Smik, Lukas [Rapid Communications in Mass Spectrometry, 2020, vol. 34, # 15]

22
[ 150-86-7 ]
[ 189302-44-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogen In ethanol for 72h;
100%	With hydrogen In ethanol at 20℃; for 72h;
96%	With platinum(IV) oxide; hydrogen In tetrahydrofuran at 20℃; for 4h;	AA14 Molecule A27: Product Obtained by Hydrogenation of Phytol Platinum oxide (PtO2, 1.15 g, 6.61 mmol) is added to a solution of phytol (30.00 g, 101.20 mmol) in THF (450 mL) under argon, and the mixture is placed under 1 bar of dihydrogen, then stirred for 4 h at ambient temperature. After filtration through celite rinsing with THF, a black oil of molecule A27 is obtained by concentration at reduced pressure.Yield: 29.00 g (96%).1H NMR (CDCl3, ppm): 0.84 (6H); 0.86 (6H); 0.89 (3H); 1.00-1.46 (22H); 1.46-1.68 (3H); 3.61-3.73 (2H).

95%	With hydrogen In ethanol for 72h;
92%	With <(S)-BINAP>chloro(p-cymene)ruthenium chloride; hydrogen In methanol for 96h; Ambient temperature; 90 kgf/cm²;
89%	With hydrazine hydrate; propionic acid In ethanol at 50 - 60℃; for 312h;
48%	With hydrogen
	With hydrogen
	Multi-step reaction with 3 steps 1: MnO₂ 2: (i), (ii) MnO₂, AcOH 3: (i) (hydroboration), (ii) H₂O₂, Na₂CO₃
	Multi-step reaction with 3 steps 1: MnO₂ 2: (i), (ii) MnO₂, AcOH 3: (i) (hydroboration), (ii) H₂O₂, Na₂CO₃
	Multi-step reaction with 4 steps 1: MnO₂ 2: AgNO₃ 4: (i) (hydroboration), (ii) H₂O₂, Na₂CO₃
	Multi-step reaction with 4 steps 1: MnO₂ 2: AgNO₃ 4: (i) (hydroboration), (ii) H₂O₂, Na₂CO₃
	Multi-step reaction with 3 steps 1: MnO₂ 2: AgNO₃ 3: (i) (hydroboration), (ii) H₂O₂, Na₂CO₃
	Multi-step reaction with 3 steps 1: MnO₂ 2: AgNO₃ 3: (i) (hydroboration), (ii) H₂O₂, Na₂CO₃
	Multi-step reaction with 2 steps 1: MnO₂ 2: (i) (hydroboration), (ii) H₂O₂, Na₂CO₃
	Multi-step reaction with 2 steps 1: MnO₂ 2: (i) (hydroboration), (ii) H₂O₂, Na₂CO₃
	Multi-step reaction with 3 steps 1: HBr 2: acetone 3: (i) (hydroboration), (ii) H₂O₂, Na₂CO₃
	Multi-step reaction with 3 steps 1: HBr 2: acetone 3: (i) (hydroboration), (ii) H₂O₂, Na₂CO₃
	Multi-step reaction with 2 steps 1: HBr 2: (i) (hydroboration), (ii) H₂O₂, Na₂CO₃
	Multi-step reaction with 2 steps 1: HBr 2: (i) (hydroboration), (ii) H₂O₂, Na₂CO₃
	With hydrogen In tetrahydrofuran for 24h;	1 To a solution of 1.00 g phytol in dry tetrahydrofuran was added 0.10 g 5% palladium on carbon. The mixture was allowed to stir 24 h under hydrogen at 1 atm. The catalyst was removed by centrifugation and the solvent was then removed by rotary evaporation. The resulting oil was purified by molecular distillation at about 100° C. and 0.1 mm Hg to give a colorless oil
	In methanol	R.1 Synthesis of 2,3-dihydrophytol Reference Example 1 Synthesis of 2,3-dihydrophytol Phytol (10.00 g, 33.7 mmol) was dissolved in methanol, Pt/C (2%, 1.00 g) was suspended therein and the suspension was stirred overnight under a hydrogen atmosphere. After completion of the reaction, the suspension was filtered to remove Pt/C, and the filtrate was concentrated to give 2,3-dihydrophytol. This was used for the next reaction without purification. 1H-NMR (300 MHz): δ 0.80-0.93 (15H, m, Me), 0.98-1.70 (24H, br, m, Me2CH-[C3H6-CHMe]3-CH2CH2-OH), 3.62-3.75 (2H, -CH2-OH).
	In methanol	P.1 Synthesis of 2,3-dihydrophytol Preparation Example 1 Synthesis of 2,3-dihydrophytol Phytol (10.00 g, 33.7 mmol) was dissolved in methanol, Pt/C (2%, 1.00 g) was suspended therein and the suspension was stirred overnight under a hydrogen atmosphere. After completion of the reaction, the suspension was filtered to remove Pt/C, and the filtrate was concentrated to give 2,3-dihydrophytol. This was used for the next reaction without purification.
	With hydrogen; nickel Autoclave;
	With 2 % platinum on carbon; hydrogen In methanol	1 Preparation Example 1: Synthesis of 2,3-dihydrophytol Phytol (10.00 g, 33.7 mmol) was dissolved in methanol, Pt/C (2%, 1.00 g) was suspended therein and the suspension was stirred overnight under a hydrogen atmosphere. After completion of the reaction, the suspension was filtered to remove Pt/C, and the filtrate was concentrated to give 2,3-dihydrophytol. This was used for the next reaction without purification.
	With 2 % platinum on carbon; hydrogen In methanol	1 Preparation Example 1 Synthesis of 2,3-dihydrophytol Phytol (10.00 g, 33.7 mmol) was dissolved in methanol, Pt/C (2%, 1.00 g) was suspended therein and the suspension was stirred overnight under a hydrogen atmosphere. After completion of the reaction, the suspension was filtered to remove Pt/C, and the filtrate was concentrated to give 2,3-dihydrophytol. This was used for the next reaction without purification.
	With hydrogen In ethanol at 20℃; for 72h;
	With platinum on activated charcoal; hydrogen In methanol

Reference： [1]Bendavid; Burns; Field; Hashimoto; Ridley; Sandanayake; Wieczorek [Journal of Organic Chemistry, 2001, vol. 66, # 11, p. 3709 - 3716]
[2]Location in patent: experimental part Pal, Asish; Srivastava, Aasheesh; Bhattacharya, Santanu [Chemistry - A European Journal, 2009, vol. 15, # 36, p. 9169 - 9182]
[3]Current Patent Assignee: ADOCIA - US2018/193421, 2018, A1 Location in patent: Paragraph 0675-0677
[4]Location in patent: experimental part Wang, Haitang; Wettig, Shawn D. [Physical Chemistry Chemical Physics, 2011, vol. 13, # 2, p. 637 - 642]
[5]Eguchi, Tadashi; Arakawa, Kenji; Terachi, Takumi; Kakinuma, Katsumi [Journal of Organic Chemistry, 1997, vol. 62, # 7, p. 1924 - 1933]
[6]Moss, Robert A.; Fujita, Tsunehisa [Tetrahedron Letters, 1990, vol. 31, # 52, p. 7559 - 7562]
[7]Flitsch, Sabine L.; Taylor, James P.; Turner, Nicholas J. [Journal of the Chemical Society. Chemical communications, 1991, # 6, p. 380 - 382]
[8]Bessiere-Chretien,Y.; Marion,J.P. [Bulletin de la Societe Chimique de France, 1970, p. 3013 - 3019]
[9]Bessiere-Chretien,Y.; Marion,J.P. [Bulletin de la Societe Chimique de France, 1970, p. 3013 - 3019]
[10]Bessiere-Chretien,Y.; Marion,J.P. [Bulletin de la Societe Chimique de France, 1970, p. 3013 - 3019]
[11]Bessiere-Chretien,Y.; Marion,J.P. [Bulletin de la Societe Chimique de France, 1970, p. 3013 - 3019]
[12]Bessiere-Chretien,Y.; Marion,J.P. [Bulletin de la Societe Chimique de France, 1970, p. 3013 - 3019]
[13]Bessiere-Chretien,Y.; Marion,J.P. [Bulletin de la Societe Chimique de France, 1970, p. 3013 - 3019]
[14]Bessiere-Chretien,Y.; Marion,J.P. [Bulletin de la Societe Chimique de France, 1970, p. 3013 - 3019]
[15]Bessiere-Chretien,Y.; Marion,J.P. [Bulletin de la Societe Chimique de France, 1970, p. 3013 - 3019]
[16]Bessiere-Chretien,Y.; Marion,J.P. [Bulletin de la Societe Chimique de France, 1970, p. 3013 - 3019]
[17]Bessiere-Chretien,Y.; Marion,J.P. [Bulletin de la Societe Chimique de France, 1970, p. 3013 - 3019]
[18]Bessiere-Chretien,Y.; Marion,J.P. [Bulletin de la Societe Chimique de France, 1970, p. 3013 - 3019]
[19]Bessiere-Chretien,Y.; Marion,J.P. [Bulletin de la Societe Chimique de France, 1970, p. 3013 - 3019]
[20]Bessiere-Chretien,Y.; Marion,J.P. [Bulletin de la Societe Chimique de France, 1970, p. 3013 - 3019]
[21]Current Patent Assignee: INDIANA STATE UNIVERSITY - US2005/158329, 2005, A1 Location in patent: Page/Page column 4
[22]Current Patent Assignee: AJINOMOTO COMPANY INC - US2012/59149, 2012, A1
[23]Current Patent Assignee: AJINOMOTO COMPANY INC - US2013/267697, 2013, A1 Location in patent: Page/Page column
[24]El-Ballouli, Ala'A O.; Kayal, Himadri; Shuai, Chen; Zeidan, Tarek A.; Raad, Farah S.; Leng, Siwei; Wex, Brigitte; Cheng, Stephen Z.D.; Eichhorn, S. Holger; Kaafarani, Bilal R. [Tetrahedron, 2015, vol. 71, # 2, p. 308 - 314]
[25]Current Patent Assignee: AJINOMOTO COMPANY INC - EP2816053, 2014, A1 Location in patent: Paragraph 0317
[26]Current Patent Assignee: AJINOMOTO COMPANY INC - US9371353, 2016, B2 Location in patent: Page/Page column 66
[27]Montagut-Romans, Adrien; Boulven, Manon; Jacolot, Maïwenn; Moebs-Sanchez, Sylvie; Hascoët, Claire; Hammed, Abdessalem; Besse, Stéphane; Lemaire, Marc; Benoit, Etienne; Lattard, Virginie; Popowycz, Florence [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 7, p. 1598 - 1601]
[28]Takahashi, Daisuke; Inomata, Tatsuji; Fukui, Tatsuya [Angewandte Chemie - International Edition, 2017, vol. 56, # 27, p. 7803 - 7807][Angew. Chem., 2017, vol. 129, p. 7911 - 7915,5]

23
[ 150-86-7 ]
[ 4444-13-7 ]

Yield	Reaction Conditions	Operation in experiment
86%	With pyridine; phosphorus tribromide In benzene at 4 - 35℃; for 3.5h;
86%	With phosphorus tribromide In benzene at 4 - 35℃; for 4.5h;	PhY-11(1-bromo-3, 7, 11, 15-tetramethyl-2-hexadecene) PBr3 (3 mmol) was added to solution of phytol (2 mmol) indry benzene. The reaction mixture was left at 4 °C for30 min, followed by stirring at room temperature (30-35 °C)for 3 h. After completion, the solvent was removed byevaporation, and the residue was extracted with chloroform.The combined organic extracts were dried and evaporated togive crude products, which on purification by columnchromatography on silica gel, afforded pure product 11(PhY-11) as a viscous dirty-white liquid in 86% yield(619.5 mg) (purity >95%).
	With phosphorus tribromide In pyridine

	With hydrogen bromide
	With pyridine; phosphorus tribromide In hexane at 0 - 20℃; for 3h; Inert atmosphere;	1. Synthesis of (7R,11R,E)-1-bromo-3,7,11,15-tetramethylhexadec-2-ene 6¹ To a well stirred solution of phytol (350 mg, 1.18 mmol), pyridine (48 L) and hexane (0.70 mL) under Argon atmosphere at 0° were added dropwise a solution of PBr3 (640 mg, 2.26 mmol) in hexane (0.24 mL). After stirring for 3 hours at room temperature the mixture was quenched with ice water (10 mL) and extracted with DCM (3 x 15 mL). The combined organic layers were washed with 1N HCl (10 mL), saturated NaHCO3 solution, dried over MgSO4 and concentrated in vacuo to give the desired product 6 as a colorless oil, which was used for the next step without further purification and without structure determination. HPLC: Rt = 12.09 min.
	With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; for 2h;

Reference： [1]Upadhyay, Harish C.; Dwivedi, Gaurav R.; Roy, Sudeep; Sharma, Ashok; Darokar, Mahendra P.; Srivastava, Santosh K. [ChemMedChem, 2014, vol. 9, # 8, p. 1860 - 1868]
[2]Saxena, Archana; Upadhyay, Harish C.; Cheema, Harveer S.; Srivastava, Santosh K.; Darokar, Mahendra P.; Bawankule, Dnyaneshwar U. [Medicinal Chemistry Research, 2018, vol. 27, # 5, p. 1345 - 1354]
[3]Bessiere-Chretien,Y.; Marion,J.P. [Bulletin de la Societe Chimique de France, 1970, p. 3013 - 3019]
[4]Bessiere-Chretien,Y.; Marion,J.P. [Bulletin de la Societe Chimique de France, 1970, p. 3013 - 3019]
[5]Naumann, Eva Christine; Göring, Stefan; Ogorek, Isabella; Weggen, Sascha; Schmidt, Boris [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 13, p. 3852 - 3856]
[6]Montagut-Romans, Adrien; Boulven, Manon; Jacolot, Maïwenn; Moebs-Sanchez, Sylvie; Hascoët, Claire; Hammed, Abdessalem; Besse, Stéphane; Lemaire, Marc; Benoit, Etienne; Lattard, Virginie; Popowycz, Florence [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 7, p. 1598 - 1601]

24
[ 7437-61-8 ]
[ 130627-55-3 ]
[ 150-86-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With copper(l) iodide In tetrahydrofuran at -20 - 0℃; for 24h;

Reference： [1]Fujisawa, Tamotsu; Sato, Toshio; Kawara, Tatsuo; Ohashi, Kazuo [Tetrahedron Letters, 1981, vol. 22, # 48, p. 4823 - 4826]

25
[ 2211-27-0 ]
[ 150-86-7 ]
[ 84-80-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Golubkina, N. A.; Sarycheva, I. K.; Evstigneeva, R. P.; Mikhal'chenko, O. L.; Uzakova, D. U.; Askarov, K. A. [Pharmaceutical Chemistry Journal, 1986, vol. 20, # 2, p. 126 - 128][Khimiko-Farmatsevticheskii Zhurnal, 1986, vol. 20, # 2, p. 195 - 197]

26
[ 150-86-7 ]
[ 14237-72-0 ]

Yield	Reaction Conditions	Operation in experiment
96%	With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate In nonane; dichloromethane at -20℃; for 3h; Molecular sieve; Inert atmosphere;
85%	With titanium(IV) isopropylate; Dimethyl D-tartrate; Trimethylacetic acid In dichloromethane at -20℃;
	With 3-chloro-benzenecarboperoxoic acid In dichloromethane

Reference： [1]Location in patent: experimental part Lu, Jun; Khdour, Omar M.; Armstrong, Jeffrey S.; Hecht, Sidney M. [Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 21, p. 7628 - 7638]
[2]Inoue, Seiichi; Ikeda, Hiroshi; Sato, Shuichi; Horie, Kiyohiro; Ota, Tomomi; et al. [Journal of Organic Chemistry, 1987, vol. 52, # 24, p. 5495 - 5497]
[3]Rontani [Tetrahedron Letters, 1991, vol. 32, # 45, p. 6551 - 6552]

27
[ 150-86-7 ]
[ 18654-63-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogen In methanol for 24h;

Reference： [1]Sita [Journal of Organic Chemistry, 1993, vol. 58, # 19, p. 5285 - 5287]

28
[ 108-24-7 ]
[ 150-86-7 ]
[ 10236-16-5 ]

Yield	Reaction Conditions	Operation in experiment
61%	With pyridine In hexane at 21 - 23℃; for 18h;
16 mg	With pyridine Ambient temperature;
	With pyridine

19 mg

With pyridine at 20℃;

Reference： [1]Malaise, Gregory; Bonrath, Werner; Breuninger, Manfred; Netscher, Thomas [Helvetica Chimica Acta, 2006, vol. 89, # 4, p. 797 - 812]
[2]Langenbahn, Ulrich; Burkhardt, Gunther; Becker, Hans [Phytochemistry, 1993, vol. 33, # 5, p. 1173 - 1180]
[3]Itoh, Daisuke; Karunagoda, Renuka Praxide; Fushie, Takashi; Katoh, Kenji; Nabeta, Kensuke [Journal of Natural Products, 2000, vol. 63, # 8, p. 1090 - 1093]
[4]Bhattacharya, Asish K; Rana, Kalpeshkumar C [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 7, p. 901 - 903]

29
[ 92116-50-2 ]
[ 150-86-7 ]

Yield	Reaction Conditions	Operation in experiment
68%	With hydrogenchloride; ammonium chloride In tetrahydrofuran at 0 - 20℃; for 3h;

Reference： [1]Gramatica, Paola; Manitto, Paolo; Monti, Diego; Speranza, Giovanna [Tetrahedron, 1987, vol. 43, # 19, p. 4481 - 4486]

30
[ 66432-63-1 ]
[ 150-86-7 ]

Yield	Reaction Conditions	Operation in experiment
94%	With pyridinium p-toluenesulfonate In ethanol at 55℃; for 1.5h;

Reference： [1]Schmid; Gerber; Hirth [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 684 - 702]

31
[ 150-86-7 ]
[ 74-88-4 ]
[ 66432-64-2 ]

Yield	Reaction Conditions	Operation in experiment
82%	With sodium hydride In N,N-dimethyl-formamide Ambient temperature;

Reference： [1]Schmid; Gerber; Hirth [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 684 - 702]

32
[ 111-14-8 ]
[ 150-86-7 ]
phytyl heptanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64.8%	With dmap; dicyclohexyl-carbodiimide In dichloromethane Heating;

Reference： [1]Zulueta; Tada; Ragasa [Phytochemistry, 1995, vol. 38, # 6, p. 1449 - 1450]

33
[ 150-86-7 ]
(3-methyl-3-((4R,8R)-4,8,12-trimethyltridecyl)oxiran-2-yl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With 3-chloro-benzenecarboperoxoic acid In chloroform for 0.75h;
55%	With methyl hexanoate; CpLIP₂ Y₁₇₉F (ipase/acyltransferase) from Candida parapsilosis; dihydrogen peroxide In aq. phosphate buffer; water at 20℃; Enzymatic reaction;
	With dihydrogen peroxide; methyltrioxorhenium(VII) In aq. phosphate buffer at 20℃; for 3h;

Reference： [1]Rajab, Mohamed S.; Cantrell, Charles L.; Franzblau, Scott G.; Fischer, Nikolaus H. [Planta Medica, 1998, vol. 64, # 1, p. 2 - 4]
[2]Re, Rebecca N.; Proessdorf, Johanna C.; La Clair, James J.; Subileau, Maeva; Burkart, Michael D. [Organic and Biomolecular Chemistry, 2019, vol. 17, # 43, p. 9418 - 9424]
[3]Fong, Darryl; Swager, Timothy M. [Journal of the American Chemical Society, 2021]

34
[ 150-86-7 ]
[ 207979-20-2 ]

Yield	Reaction Conditions	Operation in experiment
	With deuteromethanol; water-d2 for 13h; Ambient temperature;

Reference： [1]Eguchi, Tadashi; Morita, Mikio; Kakinuma, Katsumi [Journal of the American Chemical Society, 1998, vol. 120, # 22, p. 5427 - 5433]

35
[ 150-86-7 ]
(7R,11R)-3,7,11,15-tetramethyl-hexadeca-3ξ,5ξ-diene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With phthalic anhydride
	With phthalic anhydride; toluene-4-sulfonic acid; benzene

Reference： [1]Crabbe et al. [Proceedings of the Chemical Society, London, 1959, p. 264] Rowland [Journal of the American Chemical Society, 1957, vol. 79, p. 5007,5010] Mayer et al. [Helvetica Chimica Acta, 1963, vol. 46, p. 664] Johnstone; Quan [Journal of the Chemical Society, 1963, p. 5706,5710]
[2]Crabbe et al. [Proceedings of the Chemical Society, London, 1959, p. 264] Rowland [Journal of the American Chemical Society, 1957, vol. 79, p. 5007,5010] Mayer et al. [Helvetica Chimica Acta, 1963, vol. 46, p. 664] Johnstone; Quan [Journal of the Chemical Society, 1963, p. 5706,5710]

36
[ 150-86-7 ]
[ 58864-82-7 ]

Yield	Reaction Conditions	Operation in experiment
	With phthalic anhydride
	With phthalic anhydride; toluene-4-sulfonic acid; benzene

Reference： [1]Crabbe et al. [Proceedings of the Chemical Society, London, 1959, p. 264] Rowland [Journal of the American Chemical Society, 1957, vol. 79, p. 5007,5010] Mayer et al. [Helvetica Chimica Acta, 1963, vol. 46, p. 664] Johnstone; Quan [Journal of the Chemical Society, 1963, p. 5706,5710]
[2]Crabbe et al. [Proceedings of the Chemical Society, London, 1959, p. 264] Rowland [Journal of the American Chemical Society, 1957, vol. 79, p. 5007,5010] Mayer et al. [Helvetica Chimica Acta, 1963, vol. 46, p. 664] Johnstone; Quan [Journal of the Chemical Society, 1963, p. 5706,5710]

37
[ 150-86-7 ]
[ 645-72-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With hydrogen In ethanol; water at 20℃; for 72h;
90%	With platinum(IV) oxide hydrate; hydrogen; sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;
82.3%	With hydrogen In ethanol	8 Preparation of dihydrophytol EXAMPLE 8 Preparation of dihydrophytol Phytol (30.0 g, 0.101 mol) was dissolved in 200 ml of ethanol. A suspension of 1.8 g of Raney-Ni (W-1) in 5 ml of ethanol was added thereto, and hydrogenation was carried out under hydrogen for about 5 hours so that 2405 ml of hydrogen (theoretical volume at 24° C.; 2465 ml) was absorbed. After filtering off the catalyst through a filter paper, the ethanol was evaporated. Yield 29.9 g. Silica gel column chromatography with benzene-hexane (1:1) gave 24.7 g of the title compound (yield 82.3%).

With hydrogen In ethanol for 5h;

Reference： [1]Ishchenko, Andrii; Peng, Lingling; Zinovev, Egor; Vlasov, Alexey; Lee, Sung Chang; Kuklin, Alexander; Mishin, Alexey; Borshchevskiy, Valentin; Zhang, Qinghai; Cherezov, Vadim [Crystal Growth and Design, 2017, vol. 17, # 6, p. 3502 - 3511]
[2]Malwal, Satish R.; Chen, Lu; Hicks, Hunter; Qu, Fiona; Liu, Weidong; Shillo, Alli; Law, Wen Xuan; Zhang, Jianan; Chandnani, Neal; Han, Xu; Zheng, Yingying; Chen, Chun-Chi; Guo, Rey-Ting; Abdelkhalek, Ahmed; Seleem, Mohamed N.; Oldfield, Eric [Journal of Medicinal Chemistry, 2019, vol. 62, # 5, p. 2564 - 2581]
[3]Current Patent Assignee: NISSHIN SEIFUN GROUP INC - US4221810, 1980, A
[4]Jenisch-Anton, Angela; Mikolajczak, Andrea; Rabenstein, Andreas; Klindworth, Jutta; Fischer, Ulrich; Michaelis, Walter [Biodegradation, 1999, vol. 10, # 6, p. 383 - 392]

38
[ 150-86-7 ]
2-chloro-3,7,11,15-tetramethylhexadecan-1,3-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With 1,3,5-trichloro-2,4,6-triazine; 4-methylmorpholine N-oxide In chloroform at -10 - 20℃;

Reference： [1]Rosenau, Thomas; Potthast, Antje; Kosma, Paul [Tetrahedron, 2002, vol. 58, # 49, p. 9809 - 9815]

39
[ 150-86-7 ]
[ 112-67-4 ]
trans-palmitoylphytol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With pyridine; dmap at 30 - 35℃; for 14h;
85%	With triethylamine In hexane at 80℃; for 2h;
	With pyridine; dmap at 30 - 35℃; for 14h;	General procedure for synthesizing phytol (PhY)derivatives 1-10 General procedure: Phytol (592 mg, 2 mmol) was dissolved in dry pyridine, andthe respective acyl/aryl chloride (3 mmol) was added. Afteradding a catalytic amount of 4-dimethylaminopyridine(DMAP), the reaction mixture was stirred at 30-35 °C for14 h. After completion of the reaction, crushed ice wasadded, and the reaction mixture was extracted withchloroform (3 × 25 mL). The combined chloroform extractwas washed with 6% aqueous HCl solution to remove thepyridine. Finally, the combined CHCl3 extract was washedwith distilled water and dried over anhydrous Na2SO4, andthe solvent was removed under vacuum. The resulting crudeproducts were separately purified by column chromatography(silica gel, 60-120 mesh, 24 g, column diameter2 × 30 cm) to afford the respective derivatives, 1-10, in highpurity (>95%).

Reference： [1]Upadhyay, Harish C.; Dwivedi, Gaurav R.; Roy, Sudeep; Sharma, Ashok; Darokar, Mahendra P.; Srivastava, Santosh K. [ChemMedChem, 2014, vol. 9, # 8, p. 1860 - 1868]
[2]Pereira, Alberto S.; Siqueira, Denilson S.; Elias, Vladimir O.; Simoneit, Bernd R. T.; Cabral, Jose A.; Neto, Francisco R. Aquino [Phytochemistry, 2002, vol. 61, # 6, p. 711 - 719]
[3]Saxena, Archana; Upadhyay, Harish C.; Cheema, Harveer S.; Srivastava, Santosh K.; Darokar, Mahendra P.; Bawankule, Dnyaneshwar U. [Medicinal Chemistry Research, 2018, vol. 27, # 5, p. 1345 - 1354]

40
[ 679841-68-0 ]
[ 150-86-7 ]

Yield	Reaction Conditions	Operation in experiment
67%	With lithium aluminium tetrahydride In diethyl ether Heating;

Reference： [1]Fleming, Ian; Maiti, Pranab; Ramarao, Chandrashekar [Organic and Biomolecular Chemistry, 2003, vol. 1, # 22, p. 3989 - 4004]

41
[ 2211-27-0 ]
[ 150-86-7 ]
[ 50281-47-5 ]

Yield	Reaction Conditions	Operation in experiment
47%	With boron trifluoride diethyl etherate In 1,4-dioxane; ethyl acetate at 50℃; for 3h;
37.9%	With boron trifluoride diethyl etherate In diethyl ether at 80℃; for 2h;	5 Synthesis of 2-Methyl-3-phytyl-1,4-naphthohydroquinone Monoacetate (5) 2-Methyl- 1 ,4-naphthohydroquinone Monoacetate (4) (6 g), phytol (12.4 g) and BF3"OEt2 (0.78 g) were dissolved in ether (18 g) and heated to 80°C for 2 hrs. Ether was removed by concentrated. MeOH (9 g) was added and extracted with Heptane (30 g). The organic layer was concentrated and purified by column chromatography (Heptan:ethyl acetate system), thereby obtaining 5.0 g the title compound (Yield: 37.9%, HPLC purity: 99.9%).
37.9%	With boron trifluoride diethyl etherate In diethyl ether at 80℃; for 2h;	5 Synthesis of 2-methyl-3-phytyl-1,4-naphthohydroquinone monoacetate 2-Methyl- 1 ,4-naphthohydroquinone Monoacetate (4) (6 g), phytol (12.4 g) and BF3"OEt2 (0.78 g) were dissolved in ether (18 g) and heated to 80°C for 2 hrs. Ether was removed by concentrated. MeOH (9 g) was added and extracted with Heptane (30 g). The organic layer was concentrated and purified by column chromatography (Heptan:ethyl acetate system), thereby obtaining 5.0 g the title compound (Yield: 37.9%, HPLC purity: 99.9%).

Reference： [1]Suhara, Yoshitomo; Kamao, Maya; Tsugawa, Naoko; Okano, Toshio [Analytical Chemistry, 2005, vol. 77, # 3, p. 757 - 763]
[2]Current Patent Assignee: SUNNY PHARMTECH - WO2016/60670, 2016, A1 Location in patent: Paragraph 0052-0054
[3]Current Patent Assignee: SUNNY PHARMTECH - TW2016/15603, 2016, A Location in patent: Paragraph 0066-0068

42
[ 150-86-7 ]
[ 199484-75-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 100 percent / H₂ / Raney nickel / ethanol / 72 h 2: 87.5 g / HBr; H₂SO₄ / H₂O / 6 h / Heating
	Multi-step reaction with 2 steps 1: 89 percent / hydrazine hydrate, propionic acid / ethanol / 312 h / 50 - 60 °C 2: 81 percent / 47 percent aq. HBr, H₂SO₄ / 5.5 h / 140 °C
	Multi-step reaction with 2 steps 1: nickel; hydrogen / 2068.65 Torr / Autoclave 2: sulfuric acid; hydrogen bromide / Inert atmosphere

	Multi-step reaction with 2 steps 1: 2 % platinum on carbon; hydrogen / methanol 2: sulfuric acid; hydrogen bromide / water / 100 °C
	Multi-step reaction with 2 steps 1: 2 % platinum on carbon; hydrogen / methanol 2: hydrogen bromide; sulfuric acid / 100 °C
	Multi-step reaction with 2 steps 1: hydrogen / ethanol / 72 h / 20 °C 2: carbon tetrabromide; triphenylphosphine / dichloromethane / 2 h / 20 °C
	Multi-step reaction with 2 steps 1: platinum on activated charcoal; hydrogen / methanol 2: hydrogen bromide; sulfuric acid / 100 °C

Reference： [1]Bendavid; Burns; Field; Hashimoto; Ridley; Sandanayake; Wieczorek [Journal of Organic Chemistry, 2001, vol. 66, # 11, p. 3709 - 3716]
[2]Moss, Robert A.; Fujita, Tsunehisa [Tetrahedron Letters, 1990, vol. 31, # 52, p. 7559 - 7562]
[3]El-Ballouli, Ala'A O.; Kayal, Himadri; Shuai, Chen; Zeidan, Tarek A.; Raad, Farah S.; Leng, Siwei; Wex, Brigitte; Cheng, Stephen Z.D.; Eichhorn, S. Holger; Kaafarani, Bilal R. [Tetrahedron, 2015, vol. 71, # 2, p. 308 - 314]
[4]Current Patent Assignee: AJINOMOTO COMPANY INC - EP2816053, 2014, A1
[5]Current Patent Assignee: AJINOMOTO COMPANY INC - US9371353, 2016, B2
[6]Montagut-Romans, Adrien; Boulven, Manon; Jacolot, Maïwenn; Moebs-Sanchez, Sylvie; Hascoët, Claire; Hammed, Abdessalem; Besse, Stéphane; Lemaire, Marc; Benoit, Etienne; Lattard, Virginie; Popowycz, Florence [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 7, p. 1598 - 1601]
[7]Takahashi, Daisuke; Inomata, Tatsuji; Fukui, Tatsuya [Angewandte Chemie - International Edition, 2017, vol. 56, # 27, p. 7803 - 7807][Angew. Chem., 2017, vol. 129, p. 7911 - 7915,5]

43
[ 150-86-7 ]
[ 199484-74-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 100 percent / H₂ / Raney nickel / ethanol / 72 h 2: 87.5 g / HBr; H₂SO₄ / H₂O / 6 h / Heating 3: 81 percent / dimethylformamide / 4 h / 130 °C 4: 85 percent / H₂NNH₂*H₂O / ethanol / 2.5 h / Heating

Reference： [1]Bendavid; Burns; Field; Hashimoto; Ridley; Sandanayake; Wieczorek [Journal of Organic Chemistry, 2001, vol. 66, # 11, p. 3709 - 3716]

44
[ 150-86-7 ]
[ 199484-77-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 100 percent / H₂ / Raney nickel / ethanol / 72 h 2: 87.5 g / HBr; H₂SO₄ / H₂O / 6 h / Heating 3: 81 percent / dimethylformamide / 4 h / 130 °C 4: 85 percent / H₂NNH₂*H₂O / ethanol / 2.5 h / Heating 5: 91 percent / pyridine / 48 h / 20 °C

Reference： [1]Bendavid; Burns; Field; Hashimoto; Ridley; Sandanayake; Wieczorek [Journal of Organic Chemistry, 2001, vol. 66, # 11, p. 3709 - 3716]

45
[ 150-86-7 ]
[ 199484-76-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 100 percent / H₂ / Raney nickel / ethanol / 72 h 2: 87.5 g / HBr; H₂SO₄ / H₂O / 6 h / Heating 3: 81 percent / dimethylformamide / 4 h / 130 °C

Reference： [1]Bendavid; Burns; Field; Hashimoto; Ridley; Sandanayake; Wieczorek [Journal of Organic Chemistry, 2001, vol. 66, # 11, p. 3709 - 3716]

46
[ 150-86-7 ]
[ 199484-79-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: 100 percent / H₂ / Raney nickel / ethanol / 72 h 2.1: 87.5 g / HBr; H₂SO₄ / H₂O / 6 h / Heating 3.1: 81 percent / dimethylformamide / 4 h / 130 °C 4.1: 85 percent / H₂NNH₂*H₂O / ethanol / 2.5 h / Heating 5.1: 91 percent / pyridine / 48 h / 20 °C 6.1: 71 percent / morpho-CDI; DMAP / CH₂Cl₂ / 24 h / 20 °C 7.1: CF₃CO₂H / 2 h / 20 °C 7.2: 100 percent / K₂CO₃ / CH₂Cl₂

Reference： [1]Bendavid; Burns; Field; Hashimoto; Ridley; Sandanayake; Wieczorek [Journal of Organic Chemistry, 2001, vol. 66, # 11, p. 3709 - 3716]

47
[ 150-86-7 ]
[ 199484-78-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 100 percent / H₂ / Raney nickel / ethanol / 72 h 2: 87.5 g / HBr; H₂SO₄ / H₂O / 6 h / Heating 3: 81 percent / dimethylformamide / 4 h / 130 °C 4: 85 percent / H₂NNH₂*H₂O / ethanol / 2.5 h / Heating 5: 91 percent / pyridine / 48 h / 20 °C 6: 71 percent / morpho-CDI; DMAP / CH₂Cl₂ / 24 h / 20 °C

Reference： [1]Bendavid; Burns; Field; Hashimoto; Ridley; Sandanayake; Wieczorek [Journal of Organic Chemistry, 2001, vol. 66, # 11, p. 3709 - 3716]

48
[ 150-86-7 ]
[ 199484-80-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 100 percent / H₂ / Raney nickel / ethanol / 72 h 2: 87.5 g / HBr; H₂SO₄ / H₂O / 6 h / Heating 3: 81 percent / dimethylformamide / 4 h / 130 °C 4: 85 percent / H₂NNH₂*H₂O / ethanol / 2.5 h / Heating
	Multi-step reaction with 8 steps 1.1: 100 percent / H₂ / Raney nickel / ethanol / 72 h 2.1: 87.5 g / HBr; H₂SO₄ / H₂O / 6 h / Heating 3.1: 81 percent / dimethylformamide / 4 h / 130 °C 4.1: 85 percent / H₂NNH₂*H₂O / ethanol / 2.5 h / Heating 5.1: 91 percent / pyridine / 48 h / 20 °C 6.1: 71 percent / morpho-CDI; DMAP / CH₂Cl₂ / 24 h / 20 °C 7.1: CF₃CO₂H / 2 h / 20 °C 7.2: 100 percent / K₂CO₃ / CH₂Cl₂ 8.1: 80 percent / pyridine / 24 h / 20 °C

Reference： [1]Bendavid; Burns; Field; Hashimoto; Ridley; Sandanayake; Wieczorek [Journal of Organic Chemistry, 2001, vol. 66, # 11, p. 3709 - 3716]
[2]Bendavid; Burns; Field; Hashimoto; Ridley; Sandanayake; Wieczorek [Journal of Organic Chemistry, 2001, vol. 66, # 11, p. 3709 - 3716]

49
[ 150-86-7 ]
N-{2-[2-(2-{2-[3-(2-{2-[2-(2-benzyldisulfanylethoxy)ethoxy]ethoxy}ethylcarbamoyl)propionylamino]ethoxy}ethoxy)ethoxy]ethyl}-N'-(3,7R,11R,15-tetramethylhexadecyl)succinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 100 percent / H₂ / Raney nickel / ethanol / 72 h 2: 87.5 g / HBr; H₂SO₄ / H₂O / 6 h / Heating 3: 81 percent / dimethylformamide / 4 h / 130 °C 4: 85 percent / H₂NNH₂*H₂O / ethanol / 2.5 h / Heating 5: 18 percent / morpho-CDI; DMAP / CH₂Cl₂ / 24 h
	Multi-step reaction with 9 steps 1.1: 100 percent / H₂ / Raney nickel / ethanol / 72 h 2.1: 87.5 g / HBr; H₂SO₄ / H₂O / 6 h / Heating 3.1: 81 percent / dimethylformamide / 4 h / 130 °C 4.1: 85 percent / H₂NNH₂*H₂O / ethanol / 2.5 h / Heating 5.1: 91 percent / pyridine / 48 h / 20 °C 6.1: 71 percent / morpho-CDI; DMAP / CH₂Cl₂ / 24 h / 20 °C 7.1: CF₃CO₂H / 2 h / 20 °C 7.2: 100 percent / K₂CO₃ / CH₂Cl₂ 8.1: 80 percent / pyridine / 24 h / 20 °C 9.1: 18 percent / morpho-CDI; DMAP / CH₂Cl₂ / 24 h

Reference： [1]Bendavid; Burns; Field; Hashimoto; Ridley; Sandanayake; Wieczorek [Journal of Organic Chemistry, 2001, vol. 66, # 11, p. 3709 - 3716]
[2]Bendavid; Burns; Field; Hashimoto; Ridley; Sandanayake; Wieczorek [Journal of Organic Chemistry, 2001, vol. 66, # 11, p. 3709 - 3716]

50
[ 150-86-7 ]
[ 207979-21-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: D₂O, CH₃OD / PtO₂ / 13 h / Ambient temperature 2: 93 percent / I₂, PPh₃, imidazole / benzene / 0.5 h / Ambient temperature

Reference： [1]Eguchi, Tadashi; Morita, Mikio; Kakinuma, Katsumi [Journal of the American Chemical Society, 1998, vol. 120, # 22, p. 5427 - 5433]

51
[ 150-86-7 ]
C₂₅H₅₀⁽²⁾H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: D₂O, CH₃OD / PtO₂ / 13 h / Ambient temperature 2: 93 percent / I₂, PPh₃, imidazole / benzene / 0.5 h / Ambient temperature 3: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, a) -78 deg C, 30 min, b) -20 deg C, 30 min, 2.) THF, hexane, -78 deg C, 30 min 4: Na-Hg / tetrahydrofuran; methanol / 2.5 h / Ambient temperature 5: H₂ / 10percent Pd/C / ethyl acetate / 1.5 h

Reference： [1]Eguchi, Tadashi; Morita, Mikio; Kakinuma, Katsumi [Journal of the American Chemical Society, 1998, vol. 120, # 22, p. 5427 - 5433]

52
[ 150-86-7 ]
[2,3-2H₂]phytanyl acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: D₂O, CH₃OD / PtO₂ / 13 h / Ambient temperature 2: pyridine / 2 h / Ambient temperature

Reference： [1]Eguchi, Tadashi; Morita, Mikio; Kakinuma, Katsumi [Journal of the American Chemical Society, 1998, vol. 120, # 22, p. 5427 - 5433]

53
[ 150-86-7 ]
[6,7-2H₂]sesterterpenyl acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: D₂O, CH₃OD / PtO₂ / 13 h / Ambient temperature 2: 93 percent / I₂, PPh₃, imidazole / benzene / 0.5 h / Ambient temperature 3: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, a) -78 deg C, 30 min, b) -20 deg C, 30 min, 2.) THF, hexane, -78 deg C, 30 min 4: Na-Hg / tetrahydrofuran; methanol / 2.5 h / Ambient temperature 5: H₂ / 10percent Pd/C / ethyl acetate / 1.5 h 6: Et₃N, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

Reference： [1]Eguchi, Tadashi; Morita, Mikio; Kakinuma, Katsumi [Journal of the American Chemical Society, 1998, vol. 120, # 22, p. 5427 - 5433]

54
[ 150-86-7 ]
C₃₂H₅₆⁽²⁾H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: D₂O, CH₃OD / PtO₂ / 13 h / Ambient temperature 2: 93 percent / I₂, PPh₃, imidazole / benzene / 0.5 h / Ambient temperature 3: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, a) -78 deg C, 30 min, b) -20 deg C, 30 min, 2.) THF, hexane, -78 deg C, 30 min 4: Na-Hg / tetrahydrofuran; methanol / 2.5 h / Ambient temperature

Reference： [1]Eguchi, Tadashi; Morita, Mikio; Kakinuma, Katsumi [Journal of the American Chemical Society, 1998, vol. 120, # 22, p. 5427 - 5433]

55
[ 150-86-7 ]
[ 207979-22-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: D₂O, CH₃OD / PtO₂ / 13 h / Ambient temperature 2: 93 percent / I₂, PPh₃, imidazole / benzene / 0.5 h / Ambient temperature 3: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, a) -78 deg C, 30 min, b) -20 deg C, 30 min, 2.) THF, hexane, -78 deg C, 30 min

Reference： [1]Eguchi, Tadashi; Morita, Mikio; Kakinuma, Katsumi [Journal of the American Chemical Society, 1998, vol. 120, # 22, p. 5427 - 5433]

56
[ 150-86-7 ]
[ 184348-32-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 92 percent / H₂, <(S)-BINAP>chloro(p-cymene)uthenium chloride / methanol / 96 h / Ambient temperature; 90 kgf/cm² 2: pyridine / 2 h / 0 °C 3: 63 percent / NaH / dimethylsulfoxide / 67 h / 40 °C 4: 92 percent / H₂ / Pd-C / ethyl acetate / 29 h / 40 °C

Reference： [1]Eguchi, Tadashi; Arakawa, Kenji; Terachi, Takumi; Kakinuma, Katsumi [Journal of Organic Chemistry, 1997, vol. 62, # 7, p. 1924 - 1933]

57
[ 150-86-7 ]
2,3-bis-O-((7R,11R)-3,7,11,15-tetramethylhexadecan-1-yl)-sn-glycero-1-phosphocholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 92 percent / H₂, <(S)-BINAP>chloro(p-cymene)uthenium chloride / methanol / 96 h / Ambient temperature; 90 kgf/cm² 2: pyridine / 2 h / 0 °C 3: 63 percent / NaH / dimethylsulfoxide / 67 h / 40 °C 4: 92 percent / H₂ / Pd-C / ethyl acetate / 29 h / 40 °C 5: 2.) H₂O / 1.) pyridine, room temperature, 2 h, 2.) room temperature, 1 h, 3.) toluene, CH₃CN, 50-60 deg C, 3 d

Reference： [1]Eguchi, Tadashi; Arakawa, Kenji; Terachi, Takumi; Kakinuma, Katsumi [Journal of Organic Chemistry, 1997, vol. 62, # 7, p. 1924 - 1933]

58
[ 150-86-7 ]
[ 23315-09-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 100 percent / H₂ / <(S)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl>diacetatoruthenium(II) / methanol / 24 h / 77572.2 Torr 2: 87 percent / 48percent HBr aq., conc. H₂SO₄ / 24 h / Heating

Reference： [1]Sita [Journal of Organic Chemistry, 1993, vol. 58, # 19, p. 5285 - 5287]

59
[ 150-86-7 ]
[ 18654-64-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 100 percent / H₂ / <(S)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl>diacetatoruthenium(II) / methanol / 24 h / 77572.2 Torr 2: 85 percent / CrO₃ / acetone; aq. acetic acid / 1 h / Ambient temperature

Reference： [1]Sita [Journal of Organic Chemistry, 1993, vol. 58, # 19, p. 5285 - 5287]

60
[ 150-86-7 ]
(3R,7R,11R)-3,7,11,15-Tetramethyl-hexadecanoyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 100 percent / H₂ / <(S)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl>diacetatoruthenium(II) / methanol / 24 h / 77572.2 Torr 2: 85 percent / CrO₃ / acetone; aq. acetic acid / 1 h / Ambient temperature 3: oxalyl chloride / diethyl ether; dimethylformamide / 0.5 h / Ambient temperature

Reference： [1]Sita [Journal of Organic Chemistry, 1993, vol. 58, # 19, p. 5285 - 5287]

61
[ 150-86-7 ]
Bis<(3R,7R,11R)-3,7,11,15-tetramethyl-1-hexadecyl>sulfide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 100 percent / H₂ / <(S)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl>diacetatoruthenium(II) / methanol / 24 h / 77572.2 Torr 2: 87 percent / 48percent HBr aq., conc. H₂SO₄ / 24 h / Heating 3: 94 percent / thiourea / aq. ethanol / 3 h / Heating

Reference： [1]Sita [Journal of Organic Chemistry, 1993, vol. 58, # 19, p. 5285 - 5287]

62
[ 150-86-7 ]
[ 151054-87-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 100 percent / H₂ / <(S)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl>diacetatoruthenium(II) / methanol / 24 h / 77572.2 Torr 2: 85 percent / CrO₃ / acetone; aq. acetic acid / 1 h / Ambient temperature 3: oxalyl chloride / diethyl ether; dimethylformamide / 0.5 h / Ambient temperature 4: Et₃N / CHCl₃ / 0.5 h / Ambient temperature

Reference： [1]Sita [Journal of Organic Chemistry, 1993, vol. 58, # 19, p. 5285 - 5287]

63
[ 24529-80-4 ]
[ 150-86-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 73 percent / Ba(OH)2 / methanol 2: POCl₃ / 0.5 h 3: dimethylformamide / 3 h / 80 °C 4: 72 percent / Mg / Li₂CuCl₄ / tetrahydrofuran / 10 min, -78 deg C then 2 h, 0 deg C then 15 h, r.t. 5: 94 percent / pyridinium-p-toluolsulfonate / ethanol / 1.5 h / 55 °C
	Multi-step reaction with 5 steps 1: 73 percent / Ba(OH)2 / methanol 2: POCl₃ / 0.5 h 3: dimethylformamide / 3 h / 80 °C 4: 57 percent Chromat_. / Mg / CuI / tetrahydrofuran 5: 94 percent / pyridinium-p-toluolsulfonate / ethanol / 1.5 h / 55 °C
	Multi-step reaction with 4 steps 1: 73 percent / Ba(OH)2 / methanol 2: POCl₃ / 0.5 h 3: 48 percent Chromat_. / Mg / CuCl / tetrahydrofuran 4: 94 percent / pyridinium-p-toluolsulfonate / ethanol / 1.5 h / 55 °C

Multi-step reaction with 4 steps 1: 73 percent / Ba(OH)2 / methanol 2: POCl₃ / 0.5 h 3: 33.7 percent / Li₂CuCl₄ / tetrahydrofuran / 2 h / 0 °C 4: 94 percent / pyridinium-p-toluolsulfonate / ethanol / 1.5 h / 55 °C

Reference： [1]Schmid; Gerber; Hirth [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 684 - 702]
[2]Schmid; Gerber; Hirth [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 684 - 702]
[3]Schmid; Gerber; Hirth [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 684 - 702]
[4]Schmid; Gerber; Hirth [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 684 - 702]

64
[ 53170-97-1 ]
[ 150-86-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: POCl₃ / 0.5 h 2: dimethylformamide / 3 h / 80 °C 3: 72 percent / Mg / Li₂CuCl₄ / tetrahydrofuran / 10 min, -78 deg C then 2 h, 0 deg C then 15 h, r.t. 4: 94 percent / pyridinium-p-toluolsulfonate / ethanol / 1.5 h / 55 °C
	Multi-step reaction with 4 steps 1: POCl₃ / 0.5 h 2: dimethylformamide / 3 h / 80 °C 3: 57 percent Chromat_. / Mg / CuI / tetrahydrofuran 4: 94 percent / pyridinium-p-toluolsulfonate / ethanol / 1.5 h / 55 °C
	Multi-step reaction with 3 steps 1: POCl₃ / 0.5 h 2: 48 percent Chromat_. / Mg / CuCl / tetrahydrofuran 3: 94 percent / pyridinium-p-toluolsulfonate / ethanol / 1.5 h / 55 °C

Multi-step reaction with 3 steps 1: POCl₃ / 0.5 h 2: 33.7 percent / Li₂CuCl₄ / tetrahydrofuran / 2 h / 0 °C 3: 94 percent / pyridinium-p-toluolsulfonate / ethanol / 1.5 h / 55 °C

Reference： [1]Schmid; Gerber; Hirth [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 684 - 702]
[2]Schmid; Gerber; Hirth [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 684 - 702]
[3]Schmid; Gerber; Hirth [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 684 - 702]
[4]Schmid; Gerber; Hirth [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 684 - 702]

65
[ 55453-94-6 ]
[ 150-86-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: dimethylformamide / 3 h / 80 °C 2: 72 percent / Mg / Li₂CuCl₄ / tetrahydrofuran / 10 min, -78 deg C then 2 h, 0 deg C then 15 h, r.t. 3: 94 percent / pyridinium-p-toluolsulfonate / ethanol / 1.5 h / 55 °C
	Multi-step reaction with 3 steps 1: dimethylformamide / 3 h / 80 °C 2: 57 percent Chromat_. / Mg / CuI / tetrahydrofuran 3: 94 percent / pyridinium-p-toluolsulfonate / ethanol / 1.5 h / 55 °C
	Multi-step reaction with 2 steps 1: 48 percent Chromat_. / Mg / CuCl / tetrahydrofuran 2: 94 percent / pyridinium-p-toluolsulfonate / ethanol / 1.5 h / 55 °C

Multi-step reaction with 2 steps 1: 33.7 percent / Li₂CuCl₄ / tetrahydrofuran / 2 h / 0 °C 2: 94 percent / pyridinium-p-toluolsulfonate / ethanol / 1.5 h / 55 °C

Reference： [1]Schmid; Gerber; Hirth [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 684 - 702]
[2]Schmid; Gerber; Hirth [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 684 - 702]
[3]Schmid; Gerber; Hirth [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 684 - 702]
[4]Schmid; Gerber; Hirth [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 684 - 702]

66
[ 150-86-7 ]
[ 84-80-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: POCl₃ / 0.5 h 3: KOH / methanol; hexane; H₂O / 2 h / Ambient temperature
	Multi-step reaction with 3 steps 1: 82 percent / NaH (in oil) / dimethylformamide / Ambient temperature 3: KOH / methanol; hexane; H₂O / 2 h / Ambient temperature

Reference： [1]Schmid; Gerber; Hirth [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 684 - 702]
[2]Schmid; Gerber; Hirth [Helvetica Chimica Acta, 1982, vol. 65, # 3, p. 684 - 702]

67
[ 546-68-9 ]
aqueous 3N-K₂ CO₃ [ No CAS ]
[ 110-05-4 ]
[ 220038-45-9 ]
[ 7732-18-5 ]
[ 150-86-7 ]
(2S,3S)-epoxy-(3S,7R,11R)-3,7,11,15-tetramethylhexadecane-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	In diethyl ether; dichloromethane	8.a (a) (a) Preparation of (2S,3S)-epoxy-(3S,7R,11R)-3,7,11,15-tetramethylhexadecane-1-ol STR44 In an atmosphere of an argon stream and at -30 ° C., 1.45 ml (6.90 mmol) of D-(-)-diisopropyl tartrate and 2.05 ml (6.89 mmol) of titanium tetraisopropoxide were added to a suspension of 2.38 g of 4A molecular sieves in 20 ml of dichloromethane. After the reaction mixture was allowed to stand for 7 minutes, a solution (5.60 ml; 9.86 mmol) of t-butylperoxide (1.76 mol) in dichloromethane was added, and the whole was stirred at the same temperature for 105 minutes. Then, a solution of 2.01 g (6.77 mmol) of phytol, i.e., (3S,7R,11R)-1-hydroxy-3,7,11,15-tetramethyl-2-hexadecene (26) in 40 ml of dichloromethane, was added dropwise over 10 minutes, and the whole was stirred for 16 hours under the same conditions. Then, 6.0 ml of an aqueous 3N-K2 CO3 solution was added, and the reaction mixture was heated to a room temperature. Further, 4.0 g of celite was added 1 hour later, and the whole was stirred for 15 minutes. Then, the celite was filtered off, the filtrate was concentrated under a reduced pressure, diethyl ether and H2 O were added, and the organic layer was taken. The aqueous layer was extracted with diethyl ether. The resulting extract and the above organic layer were combined together, washed with an aqueous sodium chloride solution, and dried over magnesium sulfate. Thereafter, the solvent was evaporated under a reduced pressure to obtain 3.52 g of a crude product as a light yellow oil. The crude product was treated by column chromatography wherein 80 g of silica gel was used, and 2.00 g (yield: 95%) of the above-mentioned epoxide compound (201) was obtained as a colorless oil from the diethyl ether/n-hexane (1:4, v/v) effluent. [α]D26 =+4.44° (c=0.99, CHCl3). [α]D28 =+4.88° (c=2.80, ethyl alcohol). IR νmax (neat) cm-1: 3430, 1460, 1380, 1030, 865. H-NMR (CDCl3, δ): 0.70-1.83 (37H, m, 1H exchangeable), 2.96 (1H, dd, J=6.1 Hz, 4.6 Hz), 3.45-4.03 (2H, m), Sharp peaks: 0.83, 0.88, 0.90, 1.60. C-NMR (CDCl3, δ): 16.74 (q), 19.64 (q), 19.75 (q), 22.55 (t), 22.64 (q), 22.73 (q), 24.48 (t), 24.80 (t), 27.98 (d), 32.75 (d), 32.79 (d), 36.96 (t), 37.30 (t), 37.34 (t), 37.43 (t), 38.84 (t), 39.38 (t), 61.39 (t), 61.47 (s), 63.20 (d). MS m/z: 312 (M+), 294, 281, 250, 97, 71, 57 (100%). High-MS m/z (M+): Calculated (C20 H40 O2): 312.3028; Found: 312.3053.

Reference： [1]Current Patent Assignee: ADEKA CORP. - US5262552, 1993, A

68
[ 64-17-5 ]
[ 141-10-6 ]
[ 1604-34-8 ]
[ 150-86-7 ]

Yield	Reaction Conditions	Operation in experiment
	In water	XXIV Preparation of 6,10-Dimethyl-2-undecanone: EXAMPLE XXIV Preparation of 6,10-Dimethyl-2-undecanone: Hydrogenation of Carbon-Carbon Double Bonds in the Presence of a Ketone Catalytic hydrogenation of 6,10-dimethyl-3,5,9-undecatrien-2-one, also known as pseudoionone (17.8 g, 92.6 mmoles, purchased from Pfaltz & Bauer, Waterbury, Conn.) was effected over 5% palladium on activated carbon (1.01 g) at room temperature and 2-3 atmospheres (H2 pressure) using ethyl alcohol (50 mL) as a solvent. After 30 minutes, the catalyst was removed by filtration through a small pad of Hyflo Super-Cel filtering aid. After dilution of the filtrate with 500 mL of water, the product was isolated by extraction (3*75 mL) with hexane. The combined extracts were dried over anhydrous magnesium sulfate and filtered. Removal of the volatile organic solvents by evaporation at reduced pressure, followed by distillation, afforded 15.95 g (87% yield) of the named ketone: boiling point 68°-72° C. at 0.15 mm. The identity of this known ketone was ascertained by proton NMR analysis. For use of this ketone to prepare phytol see: F. G. Fischer and K. Lowenberg, Ann., 475, 183 (1929).

Reference： [1]Current Patent Assignee: LOYOLA UNIVERSITY CHICAGO - US5231232, 1993, A

69
[ 546-68-9 ]
[ 75-34-3 ]
[ 408332-88-7 ]
[ 150-86-7 ]
(2S,3S)-epoxy-(3S,7R,11R)-3,7,11,15-tetramethylhexadecane-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91.3%	With tert.-butylhydroperoxide; sodium hydroxide In CHCl₃ -benzene; diethyl ether; dichloromethane	1 Synthesis of (2S,3S)-epoxy-(3S,7R,11R)-3,7,11,15-tetramethylhexadecane-1-ol (formula II') EXAMPLE 1 Synthesis of (2S,3S)-epoxy-(3S,7R,11R)-3,7,11,15-tetramethylhexadecane-1-ol (formula II') A solution of 11.4 g (40 mM) of titanium tetraisopropoxide and 8.24 g (40 mM) of L-(+)-diethyl tartrate in 400 ml of dry dichloromethane was stirred at -20° C. to -30° C. in a nitrogen atmosphere. After stirring for 10 min., 12 g (40 mM) of natural phytol in 30 ml of dry dichloromethane was added and then a dichloroethane solution containing 80 mM of t-butyl hydroperoxide was added. The reaction was monitored by thin layer chromatography (tlc). (CHCl3 -benzene solvent). After stirring for 2 hours at -20° C. to -30° C., 100 ml of 10% tartric acid solution was added and the drying bath was then removed. The organic layer was separated and washed with water. The dried organic solution was concentrated under water aspirator pressure to give 12.4 g of a colorless oil. This crude product was dissolved in 300 ml of diethyl ether and 120 ml of 1 N sodium hydroxide solution was added with ice cooling. After stirring for 30 min., the organic layer was separated, washed with water and dried over magnesium sulfate. This diethyl ether solution was concentrated under water aspirator pressure to give 12.2 g of a colorless liquid. This crude material was chromatographed on 200 g of 60 to 80 mesh silica gel. Elution with n-hexane-ethyl acetate gave 11.7 g of the pure title compound (yield: 91.3%). [α]D25 =-4.4° (c 3.63 ETOH). Anal. Calcd. for C20 H40 O2 =C, 76.86%; H, 12.90%. Found: C, 77.14%; H, 12.75%. IR νcm-1 =3,400. NMR (CDCl3) δ: 0.87 (d, 6H, J=6 Hz) 1.30 (s, 3H) 2.20 (m, 1H) 2.97 (d-d, 1H) 3.48-4.00 (m, 2H). MS m/e=294.

Reference： [1]Current Patent Assignee: EISAI CO LTD - US4433159, 1984, A

70
[ 220904-29-0 ]
[ 253686-88-3 ]
[ 150-86-7 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium chloride In diethyl ether; water; ethyl acetate	2 EXAMPLE 2 Lithium aluminium hydride (0.15 g, 1 mmol) is introduced over 5 minutes into a round-bottomed flask containing anhydrous ether (50 cc) at 0° C. The mixture is stirred for 10 minutes and 3,7,11,15-tetramethyl-2-hexadecenal (0.3 g, 1 mmol) is then added in solution in anhydrous ethyl ether (5 cc). The mixture is stirred for 1 hour at 0° C. and ethyl acetate (3 cc) and water (7 cc) saturated with ammonium chloride are then added. The mixture is stirred for 15 minutes and is then extracted with ethyl ether. The organic phases are dried over magnesium sulphate. After filtering and evaporating off the solvents, 3,7,11,15-tetramethyl-2-hexadecenol (or phytol) is obtained and is characterized by its infrared spectrum and its proton nuclear magnetic resonance spectrum.

Reference： [1]Current Patent Assignee: SANOFI - US4876370, 1989, A

71
[ 150-86-7 ]
[ 1257631-81-4 ]

Yield	Reaction Conditions	Operation in experiment
88%	With hydrogen In ethanol at 20℃; for 6h;

Reference： [1]Rowinski, Pawel; Rowinska, Magdalena; Heller, Adam [Analytical Chemistry, 2008, vol. 80, # 5, p. 1746 - 1755]

72
C₁₄H₁₄O₄ [ No CAS ]
[ 150-86-7 ]
[ 1064682-67-2 ]

Yield	Reaction Conditions	Operation in experiment
35%	With boron trifluoride diethyl etherate In 1,4-dioxane; ethyl acetate at 45℃; for 3h;

Reference： [1]Suhara, Yoshitomo; Abe, Shinya; Murakami, Aya; Shimomura, Yuka; Nakagawa, Kimie; Kamao, Maya; Tsugawa, Naoko; Okano, Toshio [Tetrahedron, 2008, vol. 64, # 37, p. 8789 - 8796]

73
[ 58-27-5 ]
[ 150-86-7 ]
[ 84-80-0 ]
[ 74610-11-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 46% 2: 42%	With bis(benzonitrile)palladium(II) dichloride; tin(II) bromide In N,N-dimethyl-formamide at 50℃; for 24h;

Reference： [1]Location in patent: scheme or table Murahashi, Shun-Ichi; Fujii, Akiko; Inubushi, Yasutaka; Komiya, Naruyoshi [Tetrahedron Letters, 2010, vol. 51, # 17, p. 2339 - 2341]

74
[ 150-86-7 ]
[ 1227952-63-7 ]

Yield	Reaction Conditions	Operation in experiment
	With osmium(VIII) oxide; 4-methylmorpholine N-oxide; <i>tert</i>-butyl alcohol In tetrahydrofuran; water at 20℃; for 48h;
	With water; dihydrogen peroxide; methyltrioxorhenium(VII) In aq. phosphate buffer at 20℃; for 16h;

Reference： [1]Location in patent: experimental part Menichetti, Stefano; Amorati, Riccardo; Bartolozzi, Maria Grazia; Pedulli, Gian Franco; Salvini, Antonella; Viglianisi, Caterina [European Journal of Organic Chemistry, 2010, # 11, p. 2218 - 2225]
[2]Fong, Darryl; Swager, Timothy M. [Journal of the American Chemical Society, 2021]

75
[ 67-56-1 ]
[ 1310535-52-4 ]
[ 1310535-51-3 ]
[ 150-86-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 1.2 mg 2: 2.4 mg	Stage #1: methanol; sinocalycanchinensin C With sodium methylate at 60℃; for 24h; Stage #2: In methanol	4.7. Alkaline Hydrolysis of 3 A solution of 3 (6 mg) in 1% NaOMe-MeOH (2 mL) was heated at 60 °C with stirring for 1 day. The reaction mixture was neutralized with ion-exchange resin (Dowex 50WX8), filtered, and concentrated under reduced pressure. The residue was chromatographed over silica gel [n-hexane-acetone (9:1)] to give phytol (1.2 mg) as a colorless oil; inlMMLBox +0.7 (c 0.12, CHCl3); 1H NMR (400 MHz, CDCl3) δ 0.85, 0.86 (each 3H, d, J = 6.6 Hz, Me-18 and Me-19), 0.88 (6H, d, J = 6.5 Hz, Me-16 and Me-17), 1.68 (3H, s, Me-20), 2.00 (2H, br t, J = 6.8 Hz, H2-4), 4.16 (2H, d, J = 7.2 Hz, H2-1), 5.42 (1H, tq, J = 6.8, 1.2 Hz, H-3); 13C NMR (100 MHz, CDCl3) δ 16.2 (C-20), 19.7 (C-19), 19.7 (C-18), 22.6 (C-16), 22.7 (C-17), 24.5 (C-9), 24.8 (C-13), 25.1 (C-5), 28.0 (C-15), 32.7 (C-11), 32.8 (C-7), 36.6 (C-6), 37.3 (C-), 37.4 (C-), 37.4 (C-), 39.4 (C-14), 39.9 (C-4), 59.4 (C-1), 123.1 (C-2), 140.3 (C-3), and sinocalycanchinensin B (2) (2.4 mg).

Reference： [1]Location in patent: experimental part Kashiwada, Yoshiki; Nishimura, Kazuya; Kurimoto, Shin-Ichiro; Takaishi, Yoshihisa [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 9, p. 2790 - 2796]

76
[ 103-69-5 ]
[ 150-86-7 ]
N-ethyl-N-(3,7,11,15-tetramethylhexadecyl)aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With formic acid; C₂₈H₂₈Cl₂O₃PRuS In toluene at 150℃; for 16h; Inert atmosphere; chemoselective reaction;
65%	With tricarbonyl(η(4)-cycloocta-1,5-diene)iron In ethanol at 50℃; for 20h; Inert atmosphere; Schlenk technique; Irradiation;

Reference： [1]Sahli, Zeyneb; Sundararaju, Basker; Achard, Mathieu; Bruneau, Christian [Organic Letters, 2011, vol. 13, # 15, p. 3964 - 3967]
[2]Li, Haoquan; Achard, Mathieu; Bruneau, Christian; Sortais, Jean-Baptiste; Darcel, Christophe [RSC Advances, 2014, vol. 4, # 49, p. 25892 - 25897]

77
[ 58-27-5 ]
[ 150-86-7 ]
2,3-benzo-5-methyl-5-phytylcyclohexane-1,4-dione [ No CAS ]
[ 84-80-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 46% 2: 42%	With bis(benzonitrile)palladium(II) dichloride; tin(II) bromide In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Murahashi, Shun-Ichi; Miyaguchi, Noriko; Noda, Shinji; Naota, Takeshi; Fujii, Akiko; Inubushi, Yasutaka; Komiya, Naruyoshi [European Journal of Organic Chemistry, 2011, # 27, p. 5355 - 5365]

78
[ 1590381-01-3 ]
[ 150-86-7 ]
[ 1590381-33-1 ]

Yield	Reaction Conditions	Operation in experiment
76%	With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 20℃; for 2.1h; Inert atmosphere;	xxiv xxiv) 5-Fluoro-1-((3aR,4R,6R,6aR)-6-(((4-methoxyphenyl)diphenylmethoxy)-2,2-dipropyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-3-((7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl)pyrimidin-2,4(1H,3H)-dione (4a (E+Z)) Compound 3 (1 g; 1.59 mmol) was dissolved in anhydr. THF (10.6 ml). After addition of phytol (0.61 ml; 1.59 mmol) and Ph3P (0.62 g; 2.38 mmol) , the reaction mixture was stirred for 5 min at room temp. under N2 atmosphere and with exclusion of light. Then, the reaction mixture was cooled to 0°C, and a 40% soln. of diethylazodicarboxylate (DEAD) in toluene (0.69 ml; 2.38 mmol) was added dropwise within 1 min. After further 5 min of stirring at 0°C the mixture was allowed to warm up to room temp., and stirring was continued for 2 h. After evaporation of the solvent in high vacuo (45°C) the residue was purified by repeated chromatography on silica gel (1. column: 2 x 25 cm, EtOAc/petrolether, 1:13; 2. column: 2 x 18 cm, EtOAc/petrolether, 15:75, each solvent with 1% of Et3N). Yield 1.1 g (76%) of a colourless foam. Rf (EtOAc/petrol ether, 1:7) 0.55/0.60 (E/Z isomers). UV (MeOH): 270 (9,000). 1H-NMR ((D6)DMSO): 8.16 (d, 3J( H-C(6)cis, F) = 6.5, H-C(6)cis)); 8.25 (d, 3J(H-C(6)trans, F) = 6.5, H-C(6)trans)); 7.38 - 7.21 (m, 12H, 2 x H-C(3"), 4 x H-C(8"), 4 x H-C(9"), 2 x H-C(10")); 6.84 (d, 2H, 3J(H-C(4"), H-C(3")) = 9.0, 2 x H-C(4")); 5.84 (s, H-C(1')); 4.99 - 4.97 (m, 2H, H-C(2'), H-C(2"')); 4.67 - 4.63 (m, H-C(3'); 4.36 (d, 3J(H-C(1"')cis, H-C(2"')) = 5.0, H-C(1'")cis); 4.33 (d, 3J(H-C(1"')trans, H-C(2"')) = 5.0, H-C(1"')trans); 4.21 - 4.18 (m, H-C(4')); 3.72 (s, 3H, H3-C(6")); 3.35 - 3.32 (m, Hα-C(5')); 3.15 - 3.09 (m, Hβ-C(5')); 2.07 (t, 2H, 3J(H-C(4"')cis, H-C(5"')) = 7.5, H-C(4"')cis); 1.87 (t, 2H, 3J(H-C(4"')trans, H-C(5"')) = 7.5, H-C(4"')trans); 1.67 (s, 3H, H3C(20"')); 1.66 - 1.63 (m, 2H, H2-C(α')); 1.51 - 1.43 (m, 3H, H2-C(α), H-C(15"')); 1.42 - 1.30 (m, 6H, H2-C(β'), H2-C(5"'), H-C(7"'), H-C(11")); 1.28 - 0.98 (m, 16H, H2-C(β), H2-C(6"'), H2-C(8"'), H2-C(9"'), H2-C(10"'), H2-C(12"'), H2-C(13"'), H2-C(14"')); 0.91 (t, 3H, 2J((Ha-C(γ'), Hb-C(γ')), ((Ha-C(γ'), Hc-C(γ'))) = -7.0, H3-C(γ')); 0.84 (t, 3H, 2J((Ha-C(γ), Hb-C(γ)), ((Ha-C(γ), Hc-C(γ))) = -7.0, H3-C(γ)).0.83 - 0.78 (m, 12H, H3-C(16"'), H3-C(17"'), H3-C(18"'), H3-C(19"')). 13C-NMR ((D6)DMSO): 158.15 (C(5")); 156.09 (d, 2J(C(4), F) = -25.78, C(4); 148.60 (d, 4J(C(2), F) = 6.28, C(2)); 144.03 (C(7")); 139.35 (d, 1J(C(5), F) = 229.76, C(5)); 139.84 (s, C(3"')cis; 139.56 (s, C(3"')trans); 134.67 (C(2")); 129.86 - 126.74 (m, C(3"), C(8"), C(9"), C(10")); 125.55 (d, 2J(C(6), F) = -32.82, C(6)); 117.83 (C(2"')); 116.71 (C(Ketal)); 113.05 (C(4")); 93.22 (C(4')); 86.33 (C(1")); 85.95 (C(1')); 83.74 (C(2')); 80.82 (C(3')); 64.13 (C(5')); 54.88 (C(6")); 39.00 (C(1"')); 38.66 (C(α')); 38.54 (C(α)); 36.65-36.51(m, C(6"'), C(8"'), C(10"'), C(12"')); 35.81, 35.70 (2s, C(7"'), C(11'")); 27.25 (C(15"')); 24.27 (C(5"')); 24.01 (C(9"')); 23.62 (C(13"')); 22.41, 22.32 (2s, C(16"'), C(17"')); 19.48, 19.43 (2s, C(18"'), C(19"')); 16.88 (C(β')); 16.27 (C(β)); 15.85 (C(20"')); 14.05 (C(γ')); 14.02 (C(γ)). Anal. calc for C56H77FN2O7 (909.218): C, 73.98; H, 8.54; N, 3.08. Found : C, 73.75; H, 8.57; N, 2.73.

Reference： [1]Current Patent Assignee: B. Braun Melsungen Aktiengesellschaft - EP2712868, 2014, A1 Location in patent: Paragraph 0080

79
[ 135-19-3 ]
[ 150-86-7 ]
3-methyl-3-(4,8,12-trimethyltridecyl)-2,3-dihydro-1H-benzo[f]chromene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With iodine In chloroform for 4h; Reflux;	4.2.2 General procedure for the synthesis of chromans General procedure: In a 50 mL round bottom flask, prenyl alcohol (1.16 mmol) was mixed with chloroform (10 mL). To it, substituted phenol (4.0 equiv) and iodine (0.3 equiv) were added at room temperature. This reaction mixture was subjected to reflux with stirring for 4 h. It was then cooled to room temperature. Chloroform was directly washed with saturated solution of sodium thiosulphate followed by dilute sodium hydroxide solution. Finally chloroform layer was washed with water, dried over sodium sulfate and concentrated to furnish the crude product. This was then purified using 60-120 mesh silica gel column chromatography (hexanes/ethyl acetate) to give chroman.
76%	With iodine In chloroform for 4h; Reflux;	4.3.2.13. 3-Methyl-3-(4,8,12-trimethyltridecyl)-2,3-dihydro-1H-benzo[f]chromene (5l). A mixture of phytol (1.16 mmol), β-naphthol (4.65 mmol) and iodine (0.35 mmol) in chloroform (10 mL) was subjected to reflux with stirring for 4 h. It was then cooled to room temperature. Chloroform was directly washed with saturated solution of sodium thiosulphate followed by dilute sodium hydroxide solution. Finally chloroform layer was washed with water, dried over sodium sulfate and concentrated to furnish the crude product. This was then purified using 60-120 mesh silica gel column chromatography (hexanes/ethyl acetate, 9.8:0.2) to give 3-methyl-3-(4,8,12-trimethyltridecyl)-2,3-dihydro-1H-benzo[f]chromene (5l) (108.7 mg, 76%) as a pale yellow oil; Rf (hexanes/ethyl acetate, 9.5:0.5) 0.50; IR (neat):nmax2951, 1625, 1598, 1234 cm1; 1H NMR (CDCl3, 400 MHz):d 0.80e0.87 (m, 12H), 1.10e1.15 (m, 7H), 1.24e1.67 (m, 14H), 1.32 (s,3H), 1.89e1.99 (m, 2H), 2.99 (t, J6.8 Hz, 2H), 7.03 (d, J8.8 Hz, 1H),7.31 (t, J7.6 Hz,1H), 7.47 (t, J7.6 Hz,1H), 7.60 (d, J8.8 Hz,1H), 7.74(d, J8.0 Hz, 1H), 7.81 (d, J8.4 Hz, 1H); 13C NMR (CDCl3, 100 MHz):d 19.1 (CH2), 19.7e19.8 (3 peak tops, CH3), 21.2 (CH2), 22.7e22.8 (2peak tops, CH3), 23.9 (CH3), 24.5 (CH2), 24.8e24.9 (2 peak tops, CH2),28.0 (CH), 30.8e30.9 (2 peak tops, CH2), 32.7e32.8 (4 peak tops, CH),37.3e37.6 (6 peak tops, CH2), 39.4e39.6 (3 peak tops, CH2), 76.1 (Cq),112.6 (Cq), 119.9 (CH), 121.9 (CH), 122.9 (CH), 126.2 (CH), 127.7 (CH),128.4 (CH),128.7 (Cq),133.1 (Cq),151.4 (Cq); Anal. Calcd For C30H46O:C, 85.3; H, 10.9%; Found: C, 85.6; H, 11.1%; GCeMS: m/z calcd forC30H46O [M]: 422.68; found: 422.22.

Reference： [1]Naik, Mayuri M.; Kamat, Durga P.; Tilve, Santosh G.; Kamat, Vijayendra P. [Tetrahedron, 2014, vol. 70, # 34, p. 5221 - 5233]
[2]Naik, Mayuri M.; Kamat, Durga P.; Tilve, Santosh G.; Kamat, Vijayendra P. [Tetrahedron, 2014, vol. 70, # 34, p. 5221 - 5233]

80
[ 75-36-5 ]
[ 150-86-7 ]
[ 10236-16-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With pyridine; dmap at 30 - 35℃; for 14h;
	With pyridine; dmap at 30 - 35℃; for 14h;	General procedure for synthesizing phytol (PhY)derivatives 1-10 General procedure: Phytol (592 mg, 2 mmol) was dissolved in dry pyridine, andthe respective acyl/aryl chloride (3 mmol) was added. Afteradding a catalytic amount of 4-dimethylaminopyridine(DMAP), the reaction mixture was stirred at 30-35 °C for14 h. After completion of the reaction, crushed ice wasadded, and the reaction mixture was extracted withchloroform (3 × 25 mL). The combined chloroform extractwas washed with 6% aqueous HCl solution to remove thepyridine. Finally, the combined CHCl3 extract was washedwith distilled water and dried over anhydrous Na2SO4, andthe solvent was removed under vacuum. The resulting crudeproducts were separately purified by column chromatography(silica gel, 60-120 mesh, 24 g, column diameter2 × 30 cm) to afford the respective derivatives, 1-10, in highpurity (>95%).

Reference： [1]Upadhyay, Harish C.; Dwivedi, Gaurav R.; Roy, Sudeep; Sharma, Ashok; Darokar, Mahendra P.; Srivastava, Santosh K. [ChemMedChem, 2014, vol. 9, # 8, p. 1860 - 1868]
[2]Saxena, Archana; Upadhyay, Harish C.; Cheema, Harveer S.; Srivastava, Santosh K.; Darokar, Mahendra P.; Bawankule, Dnyaneshwar U. [Medicinal Chemistry Research, 2018, vol. 27, # 5, p. 1345 - 1354]

81
[ 17746-05-3 ]
[ 150-86-7 ]
phytyl dodecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With pyridine; dmap at 30 - 35℃; for 14h;

Reference： [1]Upadhyay, Harish C.; Dwivedi, Gaurav R.; Roy, Sudeep; Sharma, Ashok; Darokar, Mahendra P.; Srivastava, Santosh K. [ChemMedChem, 2014, vol. 9, # 8, p. 1860 - 1868]

82
[ 3282-30-2 ]
[ 150-86-7 ]
[ 127951-52-4 ]

Yield	Reaction Conditions	Operation in experiment
96%	With pyridine; dmap at 30 - 35℃; for 14h;
	With pyridine; dmap at 30 - 35℃; for 14h;	General procedure for synthesizing phytol (PhY)derivatives 1-10 General procedure: Phytol (592 mg, 2 mmol) was dissolved in dry pyridine, andthe respective acyl/aryl chloride (3 mmol) was added. Afteradding a catalytic amount of 4-dimethylaminopyridine(DMAP), the reaction mixture was stirred at 30-35 °C for14 h. After completion of the reaction, crushed ice wasadded, and the reaction mixture was extracted withchloroform (3 × 25 mL). The combined chloroform extractwas washed with 6% aqueous HCl solution to remove thepyridine. Finally, the combined CHCl3 extract was washedwith distilled water and dried over anhydrous Na2SO4, andthe solvent was removed under vacuum. The resulting crudeproducts were separately purified by column chromatography(silica gel, 60-120 mesh, 24 g, column diameter2 × 30 cm) to afford the respective derivatives, 1-10, in highpurity (>95%).

Reference： [1]Upadhyay, Harish C.; Dwivedi, Gaurav R.; Roy, Sudeep; Sharma, Ashok; Darokar, Mahendra P.; Srivastava, Santosh K. [ChemMedChem, 2014, vol. 9, # 8, p. 1860 - 1868]
[2]Saxena, Archana; Upadhyay, Harish C.; Cheema, Harveer S.; Srivastava, Santosh K.; Darokar, Mahendra P.; Bawankule, Dnyaneshwar U. [Medicinal Chemistry Research, 2018, vol. 27, # 5, p. 1345 - 1354]

83
[ 10487-71-5 ]
[ 150-86-7 ]
[ 157019-40-4 ]

Yield	Reaction Conditions	Operation in experiment
68%	With pyridine; dmap at 30 - 35℃; for 14h;
	With pyridine; dmap at 30 - 35℃; for 14h;	General procedure for synthesizing phytol (PhY)derivatives 1-10 General procedure: Phytol (592 mg, 2 mmol) was dissolved in dry pyridine, andthe respective acyl/aryl chloride (3 mmol) was added. Afteradding a catalytic amount of 4-dimethylaminopyridine(DMAP), the reaction mixture was stirred at 30-35 °C for14 h. After completion of the reaction, crushed ice wasadded, and the reaction mixture was extracted withchloroform (3 × 25 mL). The combined chloroform extractwas washed with 6% aqueous HCl solution to remove thepyridine. Finally, the combined CHCl3 extract was washedwith distilled water and dried over anhydrous Na2SO4, andthe solvent was removed under vacuum. The resulting crudeproducts were separately purified by column chromatography(silica gel, 60-120 mesh, 24 g, column diameter2 × 30 cm) to afford the respective derivatives, 1-10, in highpurity (>95%).

Reference： [1]Upadhyay, Harish C.; Dwivedi, Gaurav R.; Roy, Sudeep; Sharma, Ashok; Darokar, Mahendra P.; Srivastava, Santosh K. [ChemMedChem, 2014, vol. 9, # 8, p. 1860 - 1868]
[2]Saxena, Archana; Upadhyay, Harish C.; Cheema, Harveer S.; Srivastava, Santosh K.; Darokar, Mahendra P.; Bawankule, Dnyaneshwar U. [Medicinal Chemistry Research, 2018, vol. 27, # 5, p. 1345 - 1354]

84
[ 98-88-4 ]
[ 150-86-7 ]
1-O-benzoylphytol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With pyridine; dmap at 30 - 35℃; for 14h;

Reference： [1]Upadhyay, Harish C.; Dwivedi, Gaurav R.; Roy, Sudeep; Sharma, Ashok; Darokar, Mahendra P.; Srivastava, Santosh K. [ChemMedChem, 2014, vol. 9, # 8, p. 1860 - 1868]

85
[ 1711-05-3 ]
[ 150-86-7 ]
1-O-(m-anisoyl)phytol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With pyridine; dmap at 30 - 35℃; for 14h;
	With pyridine; dmap at 30 - 35℃; for 14h;	General procedure for synthesizing phytol (PhY)derivatives 1-10 General procedure: Phytol (592 mg, 2 mmol) was dissolved in dry pyridine, andthe respective acyl/aryl chloride (3 mmol) was added. Afteradding a catalytic amount of 4-dimethylaminopyridine(DMAP), the reaction mixture was stirred at 30-35 °C for14 h. After completion of the reaction, crushed ice wasadded, and the reaction mixture was extracted withchloroform (3 × 25 mL). The combined chloroform extractwas washed with 6% aqueous HCl solution to remove thepyridine. Finally, the combined CHCl3 extract was washedwith distilled water and dried over anhydrous Na2SO4, andthe solvent was removed under vacuum. The resulting crudeproducts were separately purified by column chromatography(silica gel, 60-120 mesh, 24 g, column diameter2 × 30 cm) to afford the respective derivatives, 1-10, in highpurity (>95%).

Reference： [1]Upadhyay, Harish C.; Dwivedi, Gaurav R.; Roy, Sudeep; Sharma, Ashok; Darokar, Mahendra P.; Srivastava, Santosh K. [ChemMedChem, 2014, vol. 9, # 8, p. 1860 - 1868]
[2]Saxena, Archana; Upadhyay, Harish C.; Cheema, Harveer S.; Srivastava, Santosh K.; Darokar, Mahendra P.; Bawankule, Dnyaneshwar U. [Medicinal Chemistry Research, 2018, vol. 27, # 5, p. 1345 - 1354]

86
[ 4521-61-3 ]
[ 150-86-7 ]
[ 127951-49-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	With pyridine; dmap at 30 - 35℃; for 14h;
	With pyridine; dmap at 30 - 35℃; for 14h;	General procedure for synthesizing phytol (PhY)derivatives 1-10 General procedure: Phytol (592 mg, 2 mmol) was dissolved in dry pyridine, andthe respective acyl/aryl chloride (3 mmol) was added. Afteradding a catalytic amount of 4-dimethylaminopyridine(DMAP), the reaction mixture was stirred at 30-35 °C for14 h. After completion of the reaction, crushed ice wasadded, and the reaction mixture was extracted withchloroform (3 × 25 mL). The combined chloroform extractwas washed with 6% aqueous HCl solution to remove thepyridine. Finally, the combined CHCl3 extract was washedwith distilled water and dried over anhydrous Na2SO4, andthe solvent was removed under vacuum. The resulting crudeproducts were separately purified by column chromatography(silica gel, 60-120 mesh, 24 g, column diameter2 × 30 cm) to afford the respective derivatives, 1-10, in highpurity (>95%).

Reference： [1]Upadhyay, Harish C.; Dwivedi, Gaurav R.; Roy, Sudeep; Sharma, Ashok; Darokar, Mahendra P.; Srivastava, Santosh K. [ChemMedChem, 2014, vol. 9, # 8, p. 1860 - 1868]
[2]Saxena, Archana; Upadhyay, Harish C.; Cheema, Harveer S.; Srivastava, Santosh K.; Darokar, Mahendra P.; Bawankule, Dnyaneshwar U. [Medicinal Chemistry Research, 2018, vol. 27, # 5, p. 1345 - 1354]

87
[ 2905-60-4 ]
[ 150-86-7 ]
1-O-(2,3-dichlorobenzoyl)phyto [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With pyridine; dmap at 30 - 35℃; for 14h;
	With pyridine; dmap at 30 - 35℃; for 14h;	General procedure for synthesizing phytol (PhY)derivatives 1-10 General procedure: Phytol (592 mg, 2 mmol) was dissolved in dry pyridine, andthe respective acyl/aryl chloride (3 mmol) was added. Afteradding a catalytic amount of 4-dimethylaminopyridine(DMAP), the reaction mixture was stirred at 30-35 °C for14 h. After completion of the reaction, crushed ice wasadded, and the reaction mixture was extracted withchloroform (3 × 25 mL). The combined chloroform extractwas washed with 6% aqueous HCl solution to remove thepyridine. Finally, the combined CHCl3 extract was washedwith distilled water and dried over anhydrous Na2SO4, andthe solvent was removed under vacuum. The resulting crudeproducts were separately purified by column chromatography(silica gel, 60-120 mesh, 24 g, column diameter2 × 30 cm) to afford the respective derivatives, 1-10, in highpurity (>95%).

Reference： [1]Upadhyay, Harish C.; Dwivedi, Gaurav R.; Roy, Sudeep; Sharma, Ashok; Darokar, Mahendra P.; Srivastava, Santosh K. [ChemMedChem, 2014, vol. 9, # 8, p. 1860 - 1868]
[2]Saxena, Archana; Upadhyay, Harish C.; Cheema, Harveer S.; Srivastava, Santosh K.; Darokar, Mahendra P.; Bawankule, Dnyaneshwar U. [Medicinal Chemistry Research, 2018, vol. 27, # 5, p. 1345 - 1354]

88
[ 102-92-1 ]
[ 150-86-7 ]
1-O-cinnamoylphytol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With pyridine; dmap at 30 - 35℃; for 14h;
	With pyridine; dmap at 30 - 35℃; for 14h;	General procedure for synthesizing phytol (PhY)derivatives 1-10 General procedure: Phytol (592 mg, 2 mmol) was dissolved in dry pyridine, andthe respective acyl/aryl chloride (3 mmol) was added. Afteradding a catalytic amount of 4-dimethylaminopyridine(DMAP), the reaction mixture was stirred at 30-35 °C for14 h. After completion of the reaction, crushed ice wasadded, and the reaction mixture was extracted withchloroform (3 × 25 mL). The combined chloroform extractwas washed with 6% aqueous HCl solution to remove thepyridine. Finally, the combined CHCl3 extract was washedwith distilled water and dried over anhydrous Na2SO4, andthe solvent was removed under vacuum. The resulting crudeproducts were separately purified by column chromatography(silica gel, 60-120 mesh, 24 g, column diameter2 × 30 cm) to afford the respective derivatives, 1-10, in highpurity (>95%).

Reference： [1]Upadhyay, Harish C.; Dwivedi, Gaurav R.; Roy, Sudeep; Sharma, Ashok; Darokar, Mahendra P.; Srivastava, Santosh K. [ChemMedChem, 2014, vol. 9, # 8, p. 1860 - 1868]
[2]Saxena, Archana; Upadhyay, Harish C.; Cheema, Harveer S.; Srivastava, Santosh K.; Darokar, Mahendra P.; Bawankule, Dnyaneshwar U. [Medicinal Chemistry Research, 2018, vol. 27, # 5, p. 1345 - 1354]

89
[ 150-86-7 ]
[ 4444-14-8 ]

Yield	Reaction Conditions	Operation in experiment
	With N-chloro-succinimide; dimethylsulfide In dichloromethane at 0 - 20℃;	57 Synthesis of mono-O-(3,7,11,15-tetramethylhexadec-2-enyl)erythritol Example 57 Synthesis of mono-O-(3,7,11,15-tetramethylhexadec-2-enyl)erythritol 0.90 g (6.7 mmol) of N-chlorosuccinimide was suspended in methylene chloride (8 mL). After addition of 0.52 mL (7.1 mmol) of dimethylsulfide at 0° C., the solution was stirred for 20 min. After addition of 1.0 g (3.4 mmol) of phytol, the mixture was stuffed for 1 hour at 0° C., and further stirred for 6 hours at room temperature. After addition of sodium bicarbonate aqueous solution, the reaction mixture was extracted with methylene chloride. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated to obtain 3,7,11,15-tetramethylhexadec-2-ene-1-chloride as a crude product.
	With N-chloro-succinimide; dimethylsulfide In dichloromethane

Reference： [1]Current Patent Assignee: FARNEX - US2016/67208, 2016, A1 Location in patent: Paragraph 0498
[2]Porta, Exequiel O. J.; Bofill Verdaguer, Ignasi; Perez, Consuelo; Banchio, Claudia; Ferreira De Azevedo, Mauro; Katzin, Alejandro M.; Labadie, Guillermo R. [MedChemComm, 2019, vol. 10, # 9, p. 1599 - 1605]

90
[ 2349-76-0 ]
[ 150-86-7 ]
5-methyl-8-(tert-butyl)tocol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With toluene-4-sulfonic acid In 1,2-dichloro-ethane for 17h; Reflux;

Reference： [1]Menichetti, Stefano; Amorati, Riccardo; Meoni, Valentina; Tofani, Lorenzo; Caminati, Gabriella; Viglianisi, Caterina [Organic Letters, 2016, vol. 18, # 21, p. 5464 - 5467]

91
2-methyl-1,4-naphthohydroquinone monopropionate [ No CAS ]
[ 150-86-7 ]
2-methyl-3-phytyl-1,4-naphthohydroquinone monopropionate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37.8%	With boron trifluoride diethyl etherate In diethyl ether at 50℃; for 3h;	6 Synthesis of 2-Methyl-3-phytyl-1,4-naphthohydroquinone Monopropionate (5a) 2-Methyl- 1 ,4-naphthohydroquinone Monopropionate (4a) (4.1 g) phytol (7.85 g) and BF3"OEt2 (0.78 g) were dissolved in ether (12 g) and heated to 50°C for 3 hrs. Ether was removed by concentrated. MeOH (4 g) was added and extracted with Heptane (20 g). The organic layer was concentrated and purified by column chromatography (Heptan:ethyl acetate system), thereby obtaining 1.7 g the title compound (Yield: 37.8%, HPLC purity: 99.9%).
37.8%	With boron trifluoride diethyl etherate In diethyl ether at 50℃; for 3h;	6 Synthesis of 2-methyl-3-phytyl-1,4-naphthohydroquinone monopropionate(5a) 2-Methyl- 1 ,4-naphthohydroquinone Monopropionate (4a) (4.1 g) phytol (7.85 g) and BF3"OEt2 (0.78 g) were dissolved in ether (12 g) and heated to 50°C for 3 hrs. Ether was removed by concentrated. MeOH (4 g) was added and extracted with Heptane (20 g). The organic layer was concentrated and purified by column chromatography (Heptan:ethyl acetate system), thereby obtaining 1.7 g the title compound (Yield: 37.8%, HPLC purity: 99.9%).

Reference： [1]Current Patent Assignee: SUNNY PHARMTECH - WO2016/60670, 2016, A1 Location in patent: Paragraph 0055-0057
[2]Current Patent Assignee: SUNNY PHARMTECH - TW2016/15603, 2016, A Location in patent: Paragraph 0069-0071

92
[ 78-39-7 ]
[ 150-86-7 ]
ethyl 3,7,11,15-tetramethyl-3-vinylhexadecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With acetic acid at 138℃;

Reference： [1]Gliszczyńska, Anna; Niezgoda, Natalia; Gladkowski, Witold; Świtalska, Marta; Wietrzyk, Joanna [PLoS ONE, 2017, vol. 12, # 2]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

CAS No. :	150-86-7	MDL No. :	MFCD00151280
Formula :	C₂₀H₄₀O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BOTWFXYSPFMFNR-PYDDKJGSSA-N
M.W :	296.53	Pubchem ID :	5280435
Synonyms :	(E)-Phytol;trans-Phytol	Chemical Name :	(7R,11R,E)-3,7,11,15-Tetramethylhexadec-2-en-1-ol

Num. heavy atoms :	21
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.9
Num. rotatable bonds :	13
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	98.94
TPSA :	20.23 Å²

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-2.29 cm/s

Log Po/w (iLOGP) :	4.77
Log Po/w (XLOGP3) :	8.19
Log Po/w (WLOGP) :	6.36
Log Po/w (MLOGP) :	5.25
Log Po/w (SILICOS-IT) :	6.57
Consensus Log Po/w :	6.23

[ CAS No. 150-86-7 ] {[proInfo.proName]}

Quality Control of [ 150-86-7 ]

Related Doc. of [ 150-86-7 ]

Product Details of [ 150-86-7 ]

Calculated chemistry of [ 150-86-7 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 150-86-7 ]

Application In Synthesis of [ 150-86-7 ]

[ 150-86-7 ] Synthesis Path-Downstream 1~92

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	1.0
Ghose :	None
Veber :	1.0
Egan :	1.0
Muegge :	2.0
Bioavailability Score :	0.55

Log S (ESOL) :	-5.98
Solubility :	0.00031 mg/ml ; 0.00000105 mol/l
Class :	Moderately soluble
Log S (Ali) :	-8.47
Solubility :	0.000000994 mg/ml ; 0.0000000034 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-5.51
Solubility :	0.000906 mg/ml ; 0.00000305 mol/l
Class :	Moderately soluble

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	4.3

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling