57-88-5

Usage

InChI:InChI=1/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1

Synthetic route

cholesteryl-2-tetrahydrofuran (70650-16-7) → cholesterol (57-88-5)

Conditions	Yield
With toluene-4-sulfonic acid In ethanol for 1h; Ambient temperature;	100%
With acetonyltriphenylphosphonium bromide In methanol; dichloromethane at 20℃; for 0.5h;	95%

3-O-(tetrahydro-2H-pyran-2-yl)cholesterol (6252-45-5) → cholesterol (57-88-5)

Conditions	Yield
poly(4-vinylpyridinium) p-toluenesulfonate In tetrahydrofuran; ethanol at 75℃; for 40h; Hydrolysis;	100%
bis(trimethylsilyl)sulphate In methanol; 1,2-dichloro-ethane at 55℃; for 0.5h;	98%
With CuCl2*H2O In ethanol for 2h; Hydrolysis; Heating;	98%

3-[(1,1-dimethylethyl)dimethylsilyl]oxycholest-5-ene (57711-50-9) → cholesterol (57-88-5)

Conditions	Yield
With aniline-terephthalaldehyde resin p-toluenesulfonic acid salt In tetrahydrofuran; methanol at 20℃; for 32h;	99%
With chloro-methylsulfanyl-methane; water; potassium iodide In 1,4-dioxane at 50℃; for 5.7h;	98%
With tetra-N-butylammonium tribromide In methanol; dichloromethane for 8h;	97%

4-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxymethyl]-benzonitrile → cholesterol (57-88-5)

Conditions	Yield
With Triethylgermyl-natrium In 1,4-dioxane; N,N,N,N,N,N-hexamethylphosphoric triamide at 50℃; for 16h;	99%

cholesterol triethylsilyl ether (7604-85-5) → cholesterol (57-88-5)

Conditions	Yield
With aniline-terephthalaldehyde resin p-toluenesulfonic acid salt In tetrahydrofuran; methanol at 20℃; for 0.166667h;	99%

cholesteryl benzoate (604-32-0) → cholesterol (57-88-5)

Conditions	Yield
With methanol; samarium(II) dibromide In tetrahydrofuran at 50℃; for 48h; Temperature;	99%

Cholesteryl acetate (604-35-3) → cholesterol (57-88-5)

Conditions	Yield
With diisobutylaluminium hydride; nickel dichloride In dichloromethane; toluene at -78℃; for 0.25h; Inert atmosphere;	98%
With potassium hydroxide In methanol at 35℃; for 1h;	97%
With aluminum oxide at 130℃; for 0.116667h; Irradiation;	96%

allyl cholesteryl ether (25092-65-3) → cholesterol (57-88-5)

Conditions	Yield
With hydridotetakis(triphenylphosphine)rhodium(I); trifluoroacetic acid In ethanol for 0.5h; Heating;	98%
With hydridotetakis(triphenylphosphine)rhodium(I); trifluoroacetic acid In ethanol for 0.5h; Product distribution; Heating; or deprotection of other allyl ethers;	98%
With diisobutylaluminium hydride; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether; toluene at 0 - 20℃; for 2h;	95%

5α,6β-dibromocholestan-3β-ol (1857-80-3) → cholesterol (57-88-5)

Conditions	Yield
With sodium selenite; rac-cysteine In tetrahydrofuran; water at 0℃; for 1h;	98%
With samarium diiodide In tetrahydrofuran for 0.333333h; Ambient temperature;	97%
With 2,2'-azobis(isobutyronitrile); diphenylstibane In toluene at 90℃; for 18h;	97%

1-((cholesteryloxy)methyl)-4-methoxybenzene (33999-75-6) → cholesterol (57-88-5)

Conditions	Yield
With trifluorormethanesulfonic acid; p-toluenesulfonamide safety-catch resin In 1,4-dioxane	98%
With trifluorormethanesulfonic acid; 1,3-Dimethoxybenzene In dichloromethane at 21℃; for 0.166667h;	91%
With silver hexafluoroantimonate; 1,2,3-trimethoxybenzene In dichloromethane at 40℃; for 10h;	85%

3β-(1-Ethoxyethoxy)-5-cholestene (54972-79-1) → cholesterol (57-88-5)

Conditions	Yield
With acetonyltriphenylphosphonium bromide In methanol; dichloromethane at 20℃; for 0.5h;	98%
With CuCl2*H2O In water; acetone Hydrolysis; Heating;	96%
With water; ammonium chloride In tetrahydrofuran at 150℃; for 1h; Glovebox; High pressure; Sealed tube;

Carbonic acid allyl ester (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester → cholesterol (57-88-5)

Conditions	Yield
With aminomethyl resin-supported N-propylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃;	98%

C28H48O → cholesterol (57-88-5)

Conditions	Yield
With sulfuric acid In 1,4-dioxane; water at 50℃; for 3h; Solvent;	97.74%

3β-hydroxycholest-5-en-23-one (27241-01-6) → cholesterol (57-88-5)

Conditions	Yield
Wolff-Kishner reduction;	97%

cholester-3β-yl thiobenzoate (34103-99-6) → cholesterol (57-88-5) + benzyl 3-cholesteryl ether (7278-60-6) + cholest-5-ene (570-74-1)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); triphenylstannane In toluene at 110℃; for 0.333333h; Yields of byproduct given;	A n/a B 97% C n/a
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In toluene at 110℃; for 0.333333h; Product distribution; Mechanism; var. of reagent, its amount;	A 38% B 49% C n/a

Carbonic acid 2-benzenesulfonyl-ethyl ester (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester (80667-96-5) → cholesterol (57-88-5)

Conditions	Yield
With triethylamine In pyridine at 20℃; for 70h; Product distribution;	96.5%

Carbonic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 2-trimethylsilanyl-ethyl ester (78687-50-0) → ethene (74-85-1) + trimethylsilyl fluoride (420-56-4) + cholesterol (57-88-5)

Conditions	Yield
With tetrabutyl ammonium fluoride In dichloromethane at 20℃; for 0.166667h; deprotection of TMSEC derivat;	A n/a B n/a C 94%

{2-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxymethoxy]-ethyl}-trimethyl-silane (76514-42-6) → cholesterol (57-88-5)

Conditions	Yield
With 4 A molecular sieve; tetrabutyl ammonium fluoride 1.) THF; 2.) DMPU, 45 deg C, 9 h;	94%
With 4 A molecular sieve; tetrabutyl ammonium fluoride Product distribution; 1.)THF; 2.) DMPU, 45 deg C, 9 h; deprotection of various ethers investigated;	94%

Carbonic acid 1-(3,5-dimethoxy-phenyl)-2-oxo-2-phenyl-ethyl ester (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester → cholesterol (57-88-5)

Conditions	Yield
In benzene for 1h; Irradiation;	94%

cholesteryl 2,2,2-trichloroethyl carbonate → cholesterol (57-88-5)

Conditions	Yield
With ammonium acetate; 10% Cd/Pd In tetrahydrofuran; water for 0.75h;	94%

sodium (20R)-5-cholesten-3β-yl sulfate (2864-50-8) → cholesterol (57-88-5)

Conditions	Yield
With toluene-4-sulfonic acid In 1,4-dioxane at 20℃; Hydrolysis;	93%

Cholesteryl-4-methoxybenzolsulfonat (77588-15-9) → cholesterol (57-88-5)

Conditions	Yield
With tetraethylammonium bromide In ethanol electrolysis at -2.1 to -2.3 V;	92.7%

cholesteryl p-toluenesulfonate (1182-65-6, 3381-56-4) → cholesterol (57-88-5)

Conditions	Yield
With tetraethylammonium bromide In ethanol electrolysis at -2.1 to -2.3 V;	92%
With sodium tetrahydroborate In diethyl ether; water; N,N-dimethyl-formamide for 6h; Ambient temperature;	86%

3β-hydroxylcholest-5,22-dien (26033-10-3, 34347-28-9, 130061-62-0, 92218-20-7) → cholesterol (57-88-5)

Conditions	Yield
With 1% Pd on activated carbon; ammonium acetate; hydrogen In ethanol at 50℃; under 2280.15 Torr; for 12h; Temperature;	91.9%
With 5%-palladium/activated carbon; hydrogen In methanol at 15 - 20℃; for 24h;	85%

3β-methoxymethoxy-5-cholestene (2626-17-7) → cholesterol (57-88-5)

Conditions	Yield
With trimethylsilyl bromide; 4 A molecular sieve In dichloromethane -30 deg C, 1 h, 0 deg C, 12 h;	91%

methanol (67-56-1) + cholesteryl oleate (1256491-32-3) → octadec-9-enoic acid methyl ester (112-62-9) + cholesterol (57-88-5)

Conditions	Yield
With potassium hydrogensulfate; silica gel at 65℃; for 10h;	A 71% B 91%

2-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-[1,4]dioxane (103846-32-8) → cholesterol (57-88-5)

Conditions	Yield
With hydrogenchloride In ethanol for 2h; Heating;	90%

3β-(2-methoxyethoxymethoxy)-5-cholestene (66168-89-6) + bis-i-propylthioboron bromide (89449-88-7) → cholesterol (57-88-5) + i-propylthiomethyl ether of cholesterol (89449-90-1)

Conditions	Yield
With dmap In dichloromethane 1.) -95 deg C, 5 min, 2.) 4-dimethylaminopyridine, -95 deg C, 15 min and -50 deg C, 10 min;	A 9% B 89%
With dmap In dichloromethane Product distribution; Mechanism; 1.) -95 deg C, 5 min, 2.) 4-dimethylaminopyridine, -95 deg C, 15 min and-50 deg C, 10 min;	A 9% B 89%

cholesterol (57-88-5) + trifluoroacetic anhydride (407-25-0) → cholesteryl trifluoroacetate (2665-02-3)

Conditions	Yield
erbium(III) triflate In acetonitrile at 20℃; for 4h;	100%

3,4-dihydro-2H-pyran (110-87-2) + cholesterol (57-88-5) → 3-O-(tetrahydro-2H-pyran-2-yl)cholesterol (6252-45-5)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane for 6h; Ambient temperature;	100%
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 1.5h;	99%
bis(trimethylsilyl)sulphate In dichloromethane; 1,2-dichloro-ethane at 0℃; for 0.333333h;	98%

cis-Octadecenoic acid (112-80-1) + cholesterol (57-88-5) → cholesterol oleate (303-43-5)

Conditions	Yield
With TiO(acac)2 In xylene for 36h; Heating;	100%
With iron(III) chloride hexahydrate In 1,3,5-trimethyl-benzene for 24h; Reflux;	99%
With iron(III)-acetylacetonate In 5,5-dimethyl-1,3-cyclohexadiene for 20h; Inert atmosphere; Reflux;	96%

6-bromohexanoic acid (4224-70-8) + cholesterol (57-88-5) → cholesteryl ω-bromohexanoate (82962-33-2)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2.33333h;	100%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h;	88%
With dmap; dicyclohexyl-carbodiimide In dichloromethane	70%

cholesterol (57-88-5) + (2S,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-chloro-6-methyltetrahydro-2H-pyran (86795-39-3) → (3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-6-methyl-tetrahydro-pyran

Conditions	Yield
With 2-methyl-but-2-ene; zinc(II) p-tert-butylbenzoate In dichloromethane for 1h; Ambient temperature;	100%

cholesterol (57-88-5) → Cholest-5-en-3-one (601-54-7)

Conditions	Yield
With C40H36Cl2FeN2P2Ru; potassium tert-butylate In toluene; tert-butyl alcohol at 145℃; for 3h; Inert atmosphere;	100%
With 1,4-butanediol dimethylacrylate crosslinked polyacenaphthylene supported t-butyl chromate In chloroform at 30℃; for 29h;	92%
With water; Dess-Martin periodane In dichloromethane for 0.5h;	91%

cholesterol (57-88-5) → Cholestanol (80-97-7)

Conditions	Yield
With hydrogen; palladium 10% on activated carbon In ethyl acetate	100%
With hydrogen; palladium dichloride In dichloromethane at 20℃; under 760 Torr;	99%
With hydrogen; palladium diacetate; pyrographite In tetrahydrofuran; methanol at 25℃; under 760.051 Torr; for 12h;	99%

cholesterol (57-88-5) + acetic anhydride (108-24-7) → Cholesteryl acetate (604-35-3)

Conditions	Yield
With iodine for 0.166667h; Ambient temperature;	100%
With toluene-4-sulfonic acid for 0.0111667h; microwave irradiation;	100%
[(nBu2Sn)12(μ3-O)14(μ2-OH)6](2+)*2C6H5SO3(1-) at 20℃; for 0.416667h;	100%

cholesterol (57-88-5) + acetic anhydride (108-24-7) → 7-ketocholesteryl acetate (809-51-8)

Conditions	Yield
With pyridine at 37℃; Inert atmosphere;	100%
With pyridine; chromium trioxide-3,5-dimethylpyrazole
Stage #1: cholesterol; acetic anhydride With dmap; triethylamine In dichloromethane at 20℃; Inert atmosphere; Stage #2: With potassium dichromate; 1-hydroxy-pyrrolidine-2,5-dione; acetic acid In acetone at 50℃; for 48h;	2.03 g

cholesterol (57-88-5) + p-toluenesulfonyl chloride (98-59-9) → cholesteryl p-toluenesulfonate (1182-65-6, 3381-56-4)

Conditions	Yield
With pyridine In chloroform at 20℃; for 12h;	100%
With pyridine at 0 - 20℃;	98%
With aluminum dodecatungstophosphate at 20℃; for 0.1h;	96%

cholesterol (57-88-5) + phenylcarbonochloridothioate (1005-56-7) → cholest-5-en-3-ol (3β)-(O-phenyl carbonothioate) (85335-71-3)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 0.833333h; Inert atmosphere;	100%
With pyridine In dichloromethane for 2h;	96%
With pyridine In chloroform-d1 at 25℃; half-life time of acylation of cholesterol with other chlorothionoformates;	84%
With pyridine In chloroform-d1 at 25℃;	84%
With sodium hydride

cholesterol (57-88-5) + α-bromopropionyl bromide (563-76-8) → (3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl 2-bromopropanoate

Conditions	Yield
With triethylamine In dichloromethane Acylation;	100%

cholesterol (57-88-5) + 2,3,4,6-tetra-O-benzoyl-1-O-trichloroacetimidoyl-α-D-galactopyranose (149707-75-5, 149707-76-6, 138479-78-4) → 1-O-cholesteryl-β-D-galactopyranoside (51704-23-5)

Conditions	Yield
Stage #1: cholesterol; 2,3,4,6-tetra-O-benzoyl-1-O-trichloroacetimidoyl-α-D-galactopyranose With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve In dichloromethane at 20℃; for 0.25h; Glycosylation; Stage #2: With sodium methylate Substitution;	100%

cholesterol (57-88-5) + C41H40Cl3NO16 → C39H66O10

Conditions	Yield
Stage #1: cholesterol; C41H40Cl3NO16 With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve In dichloromethane at 20℃; for 0.25h; Glycosylation; Stage #2: With sodium methylate Substitution;	100%

cholesterol (57-88-5) + acrylonitrile (107-13-1) → (3S,8S,9S,10R,13R,14S,17R)-3-(2-isocyanoethoxy)-10,13-dimethyl-17((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene (71507-47-6)

Conditions	Yield
With 18-crown-6 ether; potassium hydroxide In dichloromethane; water at 20℃;	100%
With water; potassium hydroxide In 1,4-dioxane at 20℃; for 120h;	100%
With N-benzyl-trimethylammonium hydroxide at 20℃; Michael Addition;	92%
With n-butyllithium; copper(I) 2-hydroxy-3-methylbenzoate; benzylamine; 1,2-bis-(diphenylphosphino)ethane In tetrahydrofuran at 4℃; for 1h; Inert atmosphere; chemoselective reaction;	54%
With 18-crown-6 ether; potassium hydroxide In dichloromethane at 20℃; for 12h; Time;

cholesterol (57-88-5) + podophyllotoxin 4-O-ortho-cyclopropylethynylbenzoate → 3-O-(epi)-podophyllotoxylcholesterol

Conditions	Yield
Stage #1: cholesterol; podophyllotoxin 4-O-ortho-cyclopropylethynylbenzoate In dichloromethane at 20℃; for 0.5h; Molecular sieve; Inert atmosphere; Stage #2: With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In dichloromethane at 20℃; for 4h; Molecular sieve; Inert atmosphere;	100%

cholesterol (57-88-5) → (6aS,6bS,9R,9aR,11aS,11bR)-9a,11b-dimethyl-9-((R)-6-methylheptan-2-yl)hexadecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxiren-3-ol (55700-78-2)

Conditions	Yield
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 1h;	99.8%
With 2,2,2-Trifluoroacetophenone; dihydrogen peroxide In acetonitrile; tert-butyl alcohol at 20℃; for 1h; Green chemistry;	99%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 1h; Ambient temperature;	97%

cholesterol (57-88-5) + 2-Methoxybenzoyl chloride (21615-34-9) → cholester-3-yl 2-methoxybenzoate

Conditions	Yield
With pyridine at 20℃; for 12h;	99.8%

cholesterol (57-88-5) + methanesulfonyl chloride (124-63-0) → cholesterol mesylate (3381-54-2)

Conditions	Yield
With pyridine at 20 - 25℃; for 20h; Inert atmosphere;	99.1%
With triethylamine In dichloromethane at 4 - 22℃; Inert atmosphere;	98%
With triethylamine In diethyl ether at 0℃; for 1h;	98%

lauric acid (143-07-7) + cholesterol (57-88-5) → cholesteryl laurate (1908-11-8)

Conditions	Yield
With iron(III) chloride hexahydrate In 1,3,5-trimethyl-benzene for 12h; Reflux;	99%
With dmap; dicyclohexyl-carbodiimide

cholesterol (57-88-5) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → cholesterol trimethylsilyl ether (1856-05-9, 16134-40-0)

Conditions	Yield
With polyvinylpolypyrrolidonium tribromide In acetonitrile at 20℃; for 0.416667h;	99%
With silica-FeCl3 at 20℃; for 0.85h; neat (no solvent);	98%
With trichloromelamine In dichloromethane; acetonitrile at 20℃; for 0.416667h;	98%

4-methyleneoxetan-2-one (674-82-8) + cholesterol (57-88-5) → (1R,3aS,3bS,7S,9aR,9bS,11aR)-9a,11a-dimethyl-1-[(2R)-6-methylheptan-2-yl]-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-yl 3-oxobutanoate (1473-23-0)

Conditions	Yield
With dmap In tetrahydrofuran at 48℃; for 0.0833333h;	99%

2,3,4,6-tetra-O-benzyl-D-glucopyranose (6564-72-3) + cholesterol (57-88-5) → cholesteryl α- and β-2,3,4,6-tetra-O-benzyl-D-glucosides (208523-33-5)

Conditions	Yield
With 4 A molecular sieve; 2-methoxyacetic acid; ytterbium(III) triflate In dichloromethane for 4h; Heating;	99%

Methyl oleate (112-62-9) + cholesterol (57-88-5) → cholesterol oleate (303-43-5)

Conditions	Yield
With iron(III)-acetylacetonate In n-heptane at 105℃; for 22h; Inert atmosphere;	99%
In hexane at 30℃; for 72h; Corynebacterium sp. S-401;	16%
With Candida rugosa lipase at 40℃; under 15.0012 - 30.0024 Torr; for 48h;
With Lipozyme IM at 80℃; under 15.0012 - 30.0024 Torr; for 48h;

cholesterol (57-88-5) → Cholest-4-en-3-one (601-57-0)

Conditions	Yield
With aluminum tris(iso-propoxide) In cyclohexanone; toluene for 10h; Reflux;	99%
With bromopentacarbonylmanganese(I); N-methyl-N,N-di(2-pyridylmethyl)amine; acetone; sodium t-butanolate In toluene at 90℃; for 24h; Inert atmosphere; Schlenk technique; Darkness;	98%
With Chromosorb; catalase; cholesterol oxidase In acetic acid butyl ester for 72h;	95%

cholesterol (57-88-5) + ethyl vinyl ether (109-92-2) → 3β-(1-Ethoxyethoxy)-5-cholestene (54972-79-1)

Conditions	Yield
With poly-p-styryl-acetonyltriphenylphosphonium bromide In dichloromethane at 20℃; for 2h;	99%
With acetonyltriphenylphosphonium bromide In dichloromethane for 0.0833333h; Ambient temperature;	97%
With pyridinium p-toluenesulfonate In dichloromethane at 0℃; for 2h;	77%
With toluene-4-sulfonic acid In dichloromethane

carbon disulfide (75-15-0) + cholesterol (57-88-5) + methyl iodide (74-88-4) → O-((3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl) S-methyl carbonodithioate (53496-46-1)

Conditions	Yield
Stage #1: cholesterol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 2h; Stage #2: carbon disulfide In tetrahydrofuran; mineral oil at 0 - 20℃; for 15h; Stage #3: methyl iodide In tetrahydrofuran; mineral oil at 0℃; for 2h;	99%
With sodium hydride	92%
Stage #1: carbon disulfide; cholesterol In dimethyl sulfoxide at 20℃; for 0.333333h; Stage #2: With N-benzyl-trimethylammonium hydroxide In dimethyl sulfoxide at 20℃; for 1h; Stage #3: methyl iodide In dimethyl sulfoxide at 20℃; for 5h;	70%

Upstream product

• 604-35-3 Cholesteryl acetate 
• 25092-65-3 allyl cholesteryl ether 
• 1857-80-3 5α,6β-dibromocholestan-3β-ol 
• 1182-65-6 cholesteryl p-toluenesulfonate 
• 2867-93-8 6β-methoxy-3α,5-cyclo-5-α-cholestane 
• 57711-50-9 3-[(1,1-dimethylethyl)dimethylsilyl]oxycholest-5-ene 
• 70650-16-7 cholesteryl-2-tetrahydrofuran 
• 6252-45-5 3-O-(tetrahydro-2H-pyran-2-yl)cholesterol 
• 54972-79-1 3β-(1-Ethoxyethoxy)-5-cholestene 
• 2864-50-8 sodium (20R)-5-cholesten-3β-yl sulfate 
• 55542-22-8 C₂₂H₃₂O₃ 
• 3464-50-4 chloroacetic acid cholesterylester 
• 124-40-3 dimethyl amine 
• 7604-85-5 cholesterol triethylsilyl ether 

Downstream Products

• 6252-45-5 Cholesterol-3-tetrahydropyranylether 
• 2930-80-5 17-(1,5-Dimethyl-hexyl)-3-iodo-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene 
• 1856-05-9 Trimethylsilylaether von Cholesterol 
• 601-54-7 cholest-5-en-3-one 
• 1510-21-0 5-cholesten-3β-ol 3-(3-carboxypropanoate) 
• 566-26-7 Cholest-5-ene-3α,7α-diol 
• 3381-54-2 Cholesteryl-methansulfonat 
• 712349-49-0 N',N''-dicyclohexyl-N-furfuryl-guanidyno(ferrocenyl)methane phosphonous acid 
• 100102-45-2 3,4,6-tri-O-benzoyl-1,2-O-cholesterylorthobenzoyl-α-D-glucopyranose 

Relevant academic research and scientific papers

Stereochemical Fate of the Isopropylidene Methyl Groups of Lanosterol during the Biosynthesis of Isofucosterol in Pinus Pinea

Lanosterol (16) was administered to Pinus pinea and the isofucosteryl acetate (6) obtained was chemically transformed into cholesterol (13).Compound (13) was incubated with rat-liver mitochondria to yield the propionic acid.The data obtained are consistent with a biosynthetic pathway in which the pro-E isopropylidene methyl group of the Δ24-precursor becomes the pro-R isopropyl methyl group in isofucosterol.

Novel Trifunctional Building Blocks for Fluorescent Polymers

(Matrix presented) Herein, we describe the synthesis of fluorescent 2-(arylsulfonyl)methacrylates and its polymers. These novel trifunctional monomers, possessing a fluorescent arylsulfonyl (ArSO2) group, an alkyl group (R), and a polymerizable olefin, serve as useful building blocks for functionalized fluorescent polymers.

Hydrolysis of Steroidal Esters Catalysed by Tetracyanoethylene

Tetracyanoethylene has been shown to be a mild catalyst which possesses some stereoselectivity, for the hydrolysis of the esters of steroidal alcohols.

Me3SI-promoted chemoselective deacetylation: a general and mild protocol

A Me3SI-mediated simple and efficient protocol for the chemoselective deprotection of acetyl groups has been developedviaemploying KMnO4as an additive. This chemoselective deacetylation is amenable to a wide range of substrates, tolerating diverse and sensitive functional groups in carbohydrates, amino acids, natural products, heterocycles, and general scaffolds. The protocol is attractive because it uses an environmentally benign reagent system to perform quantitative and clean transformations under ambient conditions.

Methods for preparing cholesterol, and derivatives and analogs thereof

The present invention relates to the field of pharmaceutical chemistry, and in particular to methods of preparing cholesterol,and derivatives and analogs thereof. The cholesterol derivatives include, but not limited to, 7-dehydrocholesterol, 25-hydroxycholesterol, 25- hydroxy7dehydrocholesterol and ergosterol. In the invention, phytosterol can be used as a raw material to prepare the compound shown in the formula I through microbial conversion, and then cholesterol and the derivatives and analogues thereof are prepared.

Novel method for synthesizing cholesterol from 21-hydroxy-20-methylpregna-4-ene-3-ketone as raw material

The invention provides a method for synthesizing cholesterol from 21-hydroxy-20-methylpregna-4-ene-3-ketone (4-BA) as a raw material. The method comprises the step of: (1) carrying out etherification reaction, oxidation reaction, Grignard reagent addition reaction, sulfonylation reaction, reduction reaction, acetylation reaction and reduction reaction on 4-BA and triethyl orthoformate to obtain cholesterol. The synthesis method is simple in process, high in yield, low in cost, environment-friendly in process and suitable for industrial production.

Method for preparing cholesterol and derivatives thereof by taking phytosterol as raw material

The invention discloses a method for preparing cholesterol and derivatives thereof by taking phytosterol as a raw material. The preparation method comprises the following steps: taking phytosterol asa starting raw material, carrying out etherification protection on 3-hydroxyl of the phytosterol, and carrying out biological fermentation, oxidation, GM-2 oxidation, witting reaction, hydrogenation and hydrolysis to obtain cholesterol and derivatives thereof. According to the invention, sterols are developed and utilized, so that the problem of raw material sources is solved, and the environmental protection problem of waste water and waste residues is also solved.

Method for synthesizing cholesterol by taking BA as raw material

The invention discloses a method for synthesizing cholesterol by taking BA as a raw material. A plant source raw material 21-hydroxy-20-methylpregna-4-en-3-one, also known as Shuangjiangchun or BA is taken as a raw material, and the cholesterol is synthesized by the steps of oxidation, Wittig reaction, acetylation, reduction, selective hydrogenation reduction and the like. The raw materials for synthesizing cholesterol are plant sources, the price is low, the safety is high, the risk of pathogenic bacteria and virus infection is avoided, and the synthesis method is easy to operate, high in yield, few in side reaction, environmentally friendly, good in economical efficiency and convenient for industrial production; and the invention solves the safety problem of the existing cholesterol product and the problems of high cost, environmental unfriendliness and unsuitability for large-scale industrial production in the synthesis technology.

PHOTOLYTIC COMPOUNDS AND TRIPLET-TRIPLET ANNIHILATION MEDIATED PHOTOLYSIS

The invention provides novel photolytic compounds and prodrugs, nanoparticles and compositions thereof, and methods of conducting photolysis mediated by triplet-triplet annihilation.

KMnO4-catalyzed chemoselective deprotection of acetate and controllable deacetylation-oxidation in one pot

A novel and efficient protocol for chemoselective deacetylation under ambient conditions was developed using catalytic KMnO4. The stoichiometric use of KMnO4 highlighted the dual role of a heterogeneous oxidant enabling direct access to aromatic aldehydes in one-pot sequential deacetylation-oxidation. The reaction employed an alternative solvent system and allowed the clean transformation of benzyl acetate to sensitive aldehyde in a single step while preventing over-oxidation to acids. Use of inexpensive and readily accessible KMnO4 as an environmentally benign reagent and the ease of the reaction operation were particularly attractive, and enabled the controlled oxidation and facile cleavage of acetate in a preceding step. This journal is