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3β,7β-cholest-5-ene-3,7-diol-3-benzoate
cholest-5-en-3β,7β-diol
Conditions | Yield |
---|---|
With sodium carbonate In methanol; water for 0.5h; Heating; | 100% |
With sodium hydroxide; tetrabutylammomium bromide In tetrahydrofuran for 48h; Heating; | 90 mg |
3β-acetoxy-7β-hydroxycholest-5-ene
cholest-5-en-3β,7β-diol
Conditions | Yield |
---|---|
With water; sodium hydroxide In ethanol; dichloromethane at 20℃; for 2h; | 95% |
With sodium carbonate In methanol; water at 25℃; Inert atmosphere; |
cholest-5-ene-3β,7β-diol diacetate
cholest-5-en-3β,7β-diol
Conditions | Yield |
---|---|
With sodium hydroxide In methanol at 20℃; Deacetylation; | 87% |
7-ketocholesteryl acetate
A
(3S,7S,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]phenanthrene-3,7-diol
B
cholest-5-en-3β,7β-diol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 65℃; for 2h; | A 80% B n/a |
With aluminum isopropoxide; isopropyl alcohol Behandeln der Reaktionsloesung mit wss. KOH bei Raumtemperatur; | |
With lithium aluminium tetrahydride |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In tetrahydrofuran; methanol at 20℃; for 2h; | 79% |
With sodium tetrahydroborate; cerium(III) chloride In tetrahydrofuran; methanol for 0.166667h; Ambient temperature; | 78% |
With sodium tetrahydroborate; cerium(III) chloride In tetrahydrofuran; methanol at 20℃; for 1h; | 75% |
With sodium tetrahydroborate; cerium(III) chloride heptahydrate In methanol at 0 - 20℃; for 4h; Inert atmosphere; | 58% |
Multi-step reaction with 3 steps 1: Et3N / CH2Cl2 / 0 °C 2: 1) 1M L-Selectride, 2) 6 M aq. NaOH, 30percent H2O2 / 1) THF, -78 deg C, 5 h, 2) THF, H2O, r.t., 1 h 3: 90 mg / nBu4NBr, 0.5 M aq. NaOH / tetrahydrofuran / 48 h / Heating View Scheme |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In dichloromethane at 23℃; for 48h; Catalytic behavior; Time; Temperature; chemoselective reaction; | A 53% B 15% |
tert.-butylhydroperoxide
cholesterol
A
7-Oxocholesterol
B
3β-hydroxycholest-5-ene-7α-hydroperoxide
C
(3S,7S,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]phenanthrene-3,7-diol
D
cholest-5-en-3β,7β-diol
E
7β-hydroperoxy-3β-hydroxycholest-5-ene
Conditions | Yield |
---|---|
Rh2(cap)4 In dichloromethane at 25℃; for 15h; Allylic oxidation; | A 30% B 10% C 12% D 3% E 4% |
cholesterol
A
7-Oxocholesterol
B
3β-hydroxycholest-5-ene-7α-hydroperoxide
C
(3S,7S,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]phenanthrene-3,7-diol
D
cholest-5-en-3β,7β-diol
E
7β-hydroperoxy-3β-hydroxycholest-5-ene
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; [Rh2(cap)4*2CH3CN] In water; 1,2-dichloro-ethane at 25℃; for 15h; | A 30% B 10% C 12% D 3% E 4% |
cholesterol
A
7-Oxocholesterol
B
cholest-5-en-3β,7β-diol
C
5beta,6beta-Epoxycholestanol
D
5α,6α-epoxycholestan-3β-ol
Conditions | Yield |
---|---|
at 150℃; Further byproducts given; | A 21.9% B 13% C 7.4% D 10.8% |
at 150℃; Further byproducts given; | A 21.9% B 13% C 7.4% D 10.8% |
at 150℃; for 1h; |
cholesterol
A
7-Oxocholesterol
B
25-hydroxychlolesterol
C
cholest-5-en-3β,7β-diol
D
5α,6α-epoxycholestan-3β-ol
Conditions | Yield |
---|---|
at 150℃; Further byproducts given; | A 21.9% B 2.3% C 13% D 10.8% |
cholesterol
A
7-Oxocholesterol
B
(3S,7S,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]phenanthrene-3,7-diol
C
cholest-5-en-3β,7β-diol
D
5α,6α-epoxycholestan-3β-ol
Conditions | Yield |
---|---|
at 150℃; Further byproducts given; | A 21.9% B 4% C 13% D 10.8% |
cholesterol
A
7-Oxocholesterol
B
cholest-5-en-3β,7β-diol
C
22(R)-Hydroxycholesterol
D
5α,6α-epoxycholestan-3β-ol
Conditions | Yield |
---|---|
at 150℃; Further byproducts given; | A 21.9% B 13% C 0.6% D 10.8% |
cholesterol
A
7-Oxocholesterol
B
cholest-5-en-3β,7β-diol
C
22-(S)-hydroxycholesterol
D
5α,6α-epoxycholestan-3β-ol
Conditions | Yield |
---|---|
at 150℃; Further byproducts given; | A 21.9% B 13% C 0.3% D 10.8% |
7-ketocholesteryl acetate
aluminum isopropoxide
isopropyl alcohol
A
(3S,7S,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]phenanthrene-3,7-diol
B
cholest-5-en-3β,7β-diol
Conditions | Yield |
---|---|
anschliessenden Behandeln mit wss.KOH; | |
anschliessenden Behandeln mit wss.KOH; |
cholesterol
A
7-Oxocholesterol
B
cholestanetriol
C
(3S,7S,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]phenanthrene-3,7-diol
D
cholest-5-en-3β,7β-diol
E
3β-hydroxycholest-5-ene-7-hydroperoxide
F
(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
Conditions | Yield |
---|---|
With egg lechitin; oxygen; tris(acetylacetonato)iron(III) In benzene at 40℃; for 24h; Product distribution; determination of fatty acid degradation, determination of stereoselectivity of epoxidation, inhibition of a radical scavenger in the oxidation, other temperature, other solvent, other catalyst; |
cholesterol
A
7-Oxocholesterol
B
cholestanetriol
C
(3S,7S,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]phenanthrene-3,7-diol
D
cholest-5-en-3β,7β-diol
E
5beta,6beta-Epoxycholestanol
F
5α,6α-epoxycholestan-3β-ol
Conditions | Yield |
---|---|
With air at 150℃; for 24h; Product distribution; var. temperature, var. time; |
cholesterol
A
Cholest-5-en-3-one
B
Cholest-4-en-3-one
C
(3S,7S,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]phenanthrene-3,7-diol
D
cholest-5-en-3β,7β-diol
E
5beta,6beta-Epoxycholestanol
F
5α,6α-epoxycholestan-3β-ol
Conditions | Yield |
---|---|
With tetrasodium 5,10,15,20-tetra(4-sulfophenyl)porphyrinatoiron(III); dihydrogen peroxide In 2,2,4-trimethylpentane; water for 12h; Product distribution; other sterols, other iron(III) porphyrins; var. water/surfactant ratio and pH; oxidation in AOT reversed micelles; |
Cholesteryl acetate
A
(3S,7S,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]phenanthrene-3,7-diol
B
cholest-5-en-3β,7β-diol
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; lithium aluminium tetrahydride; potassium carbonate; chromium(0) hexacarbonyl Yield given. Multistep reaction. Yields of byproduct given; |
5α-hydroperoxy-3β-benzoyloxycholest-6-ene
A
(3S,7S,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]phenanthrene-3,7-diol
B
cholest-5-en-3β,7β-diol
Conditions | Yield |
---|---|
With potassium hydroxide; tributyltin methoxide; triphenylphosphine Multistep reaction; |
7β-hydroperoxy-3β-hydroxycholest-5-ene
cholest-5-en-3β,7β-diol
Conditions | Yield |
---|---|
With triphenylphosphine In diethyl ether Ambient temperature; |
3β-hydroxycholest-5-ene-7-hydroperoxide
A
(3S,7S,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]phenanthrene-3,7-diol
B
cholest-5-en-3β,7β-diol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol; diethyl ether Reduction; | A n/a B 40 mg |
cholesterol
water
A
cholest-3,5-dien-7-one
B
(3S,7S,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]phenanthrene-3,7-diol
C
cholest-5-en-3β,7β-diol
Conditions | Yield |
---|---|
at 85℃; pH 8.5; |
cholesterol
water
A
cholest-3,5-dien-7-one
B
(3S,7S,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]phenanthrene-3,7-diol
C
cholest-5-en-3β,7β-diol
Conditions | Yield |
---|---|
at 85℃; pH 8.5; |
diethyl ether
7-ketocholesteryl acetate
A
(3S,7S,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]phenanthrene-3,7-diol
B
cholest-5-en-3β,7β-diol
cholesterol
A
3β,5α-dihydroxycholest-5-ene
B
(3S,7S,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]phenanthrene-3,7-diol
C
cholest-5-en-3β,7β-diol
Conditions | Yield |
---|---|
With lumiflavin; oxygen In acetonitrile for 4h; Product distribution; Further Variations:; Solvents; Reagents; reaction times; Irradiation; | A 12 mg B n/a C n/a |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 62 percent / O2; N-hydroxyphthalamide; benzoyl peroxide / ethyl acetate; acetone / 72 h / 50 - 60 °C 2: 75 percent / CeCl3*H2O; NaBH4 / tetrahydrofuran; methanol / 1 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: O2; hematoporphyrin / pyridine / 5 h / 10 °C / Irradiation 2: CHCl3 / 120 h / 20 °C 3: 40 mg / NaBH4 / methanol; diethyl ether View Scheme | |
Multi-step reaction with 4 steps 1: pyridine / dichloromethane / Inert atmosphere 2: pyridinium chlorochromate / toluene / Inert atmosphere 3: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol; tetrahydrofuran / 25 °C / Inert atmosphere 4: sodium carbonate / methanol; water / 25 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: pyridine / 37 °C / Inert atmosphere 2: lithium hydroxide / tetrahydrofuran; methanol; water / 2 h / 20 °C 3: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 4 h / 0 - 20 °C / Inert atmosphere View Scheme |
cholesterol 5α-hydroperoxide
cholest-5-en-3β,7β-diol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: CHCl3 / 120 h / 20 °C 2: 40 mg / NaBH4 / methanol; diethyl ether View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: LiALH4 / diethyl ether / 20 °C 1.2: 61 percent / pyridine / 1 h / 100 °C 2.1: 87 percent / NaOH / methanol / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: methanol; potassium carbonate / tetrahydrofuran / 1 h / 20 °C 2: sodium tetrahydroborate / methanol; tetrahydrofuran / 2 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol; tetrahydrofuran / 25 °C / Inert atmosphere 2: sodium carbonate / methanol; water / 25 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: lithium hydroxide / tetrahydrofuran; methanol; water / 2 h / 20 °C 2: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 4 h / 0 - 20 °C / Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 4h; Ambient temperature; | 95% |
Conditions | Yield |
---|---|
With 3,5-dimethyl-1H-pyrazole; pyridinium chlorochromate In dichloromethane at 2 - 3℃; for 0.5h; | 89% |
cholest-5-en-3β,7β-diol
Δ4-7β-hydroxycholesterol
Conditions | Yield |
---|---|
With phosphate buffer pH 7; oxygen; (2-hydroxypropyl)-α-cyclodextrin at 20℃; for 24h; catalase, Brevibacterium sp. cholesterol oxidase E.C. 1.1.3.6; | 85% |
With catalase; cholesterol oxidase 1.) butyl acetate, 48 h; 2.) ethanol, oxalic acid, 30 min, 60 deg C; Yield given. Multistep reaction; | |
With buffer containing Triton-X 100; cetyltrimethylammonim bromide; cholesterol oxidase In cyclohexane; butan-1-ol Kinetics; further reaction conditions; | |
With recombinant Brevibacterium cholesterol oxidase In phosphate buffer; isopropyl alcohol at 25℃; for 12h; pH=7; |
succinic acid anhydride
cholest-5-en-3β,7β-diol
cholest-5-ene-3β-7β-diyl dihemisuccinate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane for 24h; Inert atmosphere; Reflux; | 83% |
cholest-5-en-3β,7β-diol
5α-cholestane-3β,6α,7β-triol
Conditions | Yield |
---|---|
With sodium perborate tetrahydrate In tetrahydrofuran at 20℃; Inert atmosphere; | 69% |
(E)-3-(4-acetoxy-3-methoxyphenyl)acrylic acid
cholest-5-en-3β,7β-diol
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere; | 42% |
pyridine
cholest-5-en-3β,7β-diol
acetic anhydride
3β-acetoxy-7β-hydroxycholest-5-ene
Conditions | Yield |
---|---|
at 0℃; |
Conditions | Yield |
---|---|
at 180 - 190℃; |
cholest-5-en-3β,7β-diol
acetic anhydride
3β-acetoxy-7β-hydroxycholest-5-ene
Conditions | Yield |
---|---|
With pyridine at 0℃; |
cholest-5-en-3β,7β-diol
acetic anhydride
cholest-5-ene-3β,7β-diol diacetate
Conditions | Yield |
---|---|
With pyridine | |
With pyridine |
cholest-5-en-3β,7β-diol
benzoyl chloride
3β,7β-bis-benzoyloxy-cholest-5-ene
Conditions | Yield |
---|---|
With pyridine |
Conditions | Yield |
---|---|
at 180 - 190℃; |
cholest-5-en-3β,7β-diol
benzoic acid anhydride
3β,7β-cholest-5-ene-3,7-diol-3-benzoate
Conditions | Yield |
---|---|
With benzene | |
With toluene | |
With xylene |
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