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inquiry3α-Acetyloxy-12-oxo-5β-chol-9(11)-en-24-oic acid methyl ester CAS:4472-02-0 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical inter
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inquiryAnsciep Chemical is a professional enterprise manufacturing and distributing fine chemicals and speciality chemicals. We have been dedicated to heterocycle compounds and phenyl rings for tens of years. This is our mature product for export. Our quali
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inquiry5.beta.-Chol-9 (11)-en-24-oic acid, 3.alpha.-hydroxy-12-oxo-, methyl ester, acetate cas 4472-02-0Appearance:white crystalline powder Storage:Store in dry, dark and ventilated place Package:25KG drum Application:intermediate Transportation:by air, by
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inquiryfactory?direct?saleAppearance:White powder Storage:Sealed and preserved Package:200/Kilograms Application:healing drugs Transportation:By sea Port:Shanghai/tianjin
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inquiryChangzhou Extraordinary Pharmatech co., LTD. As a leading chemical manufacturer and supplier in China.DAS authentication is passed.We can provide the popular precursor chemicals, we have our own strong R & D team, have our own laboratories and fa
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inquiry5.beta.-Chol-9 (11)-en-24-oic acid, 3.alpha.-hydroxy-12-oxo-, methyl ester, acetateAppearance:Pls see the Details Storage:keep in dry and cool condition Package:25kg or according to cutomer's demand Application:Chemical research/pharma intermediate T
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methyl 3α-acetoxy-12-oxo-5β-cholan-24-oate
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
Conditions | Yield |
---|---|
With 3-iodosylbenzoic acid; diphenyl diselenide In toluene for 96h; Heating; | 89% |
With selenium(IV) oxide; acetic acid for 18h; Reflux; | 78% |
With selenium(IV) oxide; acetic acid | |
With selenium(IV) oxide; acetic acid at 180℃; for 0.5h; Temperature; Microwave irradiation; |
methyl 3α-acetoxy-5β-chol-9(11)-en-24-oate
A
C31H50O6
B
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
Conditions | Yield |
---|---|
Stage #1: methyl 3α-acetoxy-5β-chol-9(11)-en-24-oate With tert.-butylhydroperoxide; sodium hypochlorite In water; ethyl acetate at 0 - 5℃; for 7h; Stage #2: With sodium sulfite In ethyl acetate Stage #3: With pyridinium chlorochromate In ethyl acetate Product distribution / selectivity; | A n/a B 63% |
methyl 3α-acetoxy-5β-chol-9(11)-en-24-oate
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
Conditions | Yield |
---|---|
Stage #1: methyl 3α-acetoxy-5β-chol-9(11)-en-24-oate With tert.-butylhydroperoxide; sodium hypochlorite In water; ethyl acetate at 0℃; for 8 - 10h; Stage #2: With sodium sulfite In water; ethyl acetate at 50 - 55℃; for 2h; Stage #3: With pyridinium chlorochromate In ethyl acetate at 25 - 30℃; for 6 - 8h; Product distribution / selectivity; | 62% |
Stage #1: methyl 3α-acetoxy-5β-chol-9(11)-en-24-oate With tert.-butylhydroperoxide; sodium hypochlorite In water; ethyl acetate at 0 - 5℃; Stage #2: With pyridinium chlorochromate In ethyl acetate Solvent; Reagent/catalyst; Temperature; | 60.6% |
Multi-step reaction with 2 steps 1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 7 h / 0 - 5 °C 2: potassium carbonate; hydrogen / palladium on activated charcoal / dichloromethane / 24 h / 20 °C View Scheme | |
Stage #1: methyl 3α-acetoxy-5β-chol-9(11)-en-24-oate With tert.-butylhydroperoxide; sodium hypochlorite In water; ethyl acetate at 0 - 5℃; Stage #2: With pyridinium chlorochromate In ethyl acetate at 25 - 30℃; Reagent/catalyst; Solvent; Time; Temperature; | 13 g |
With chromium(VI) oxide In acetic acid at 50℃; |
C31H50O6
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; palladium on activated charcoal; potassium carbonate In dichloromethane at 20℃; for 24h; | 11% |
With hydrogen; potassium carbonate; palladium on activated charcoal In dichloromethane at 20℃; for 24h; | 11 %Chromat. |
pyridine
3α-acetoxy-11β-bromo-12-oxo-5β-cholan-24-oic acid methyl ester
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
2,4,6-trimethyl-pyridine
3α-acetoxy-11α-bromo-12-oxo-5β-cholan-24-oic acid methyl ester
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
methyl 3α-acetoxy-5β-chol-9(11)-en-24-oate
A
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
B
3α-acetoxy-9,11β-epoxy-5β,9β-cholan-24-oic acid methyl ester
Conditions | Yield |
---|---|
With potassium permanganate; acetic acid |
12α-hydroxy-3α-acetoxy-5β-cholen-(9(11))-oic acid-(24)-methyl ester
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
Conditions | Yield |
---|---|
With chromium(VI) oxide; acetic acid |
3α-acetoxy-11β-bromo-12-oxo-5β-cholan-24-oic acid methyl ester
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
Conditions | Yield |
---|---|
With pyridine |
methyl 3α-hydroxy-12-oxo-5β-chol-9(11)-en-24-oate
acetic anhydride
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
Conditions | Yield |
---|---|
With pyridine |
methyl 3α-acetoxy-5β-chol-11-ene-24-oate
N-bromoacetamide
A
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
B
methyl 3α-acetoxy-11-oxo-5β-cholan-24-oate
Conditions | Yield |
---|---|
With water; acetone Behandeln einer Loesung des Reaktionsprodukts in Chloroform und Essigsaeure mit Chrom(VI)-oxid und Erwaermen des danach isolierten Reaktionsprodukts mit Zink, Natriumacetat und Essigsaeure; | |
With water; tert-butyl alcohol Behandeln einer Loesung des Reaktionsprodukts in Chloroform und Essigsaeure mit Chrom(VI)-oxid und Erwaermen des danach isolierten Reaktionsprodukts mit Zink, Natriumacetat und Essigsaeure; |
methyl 3α-acetoxy-5β-chol-9(11)-en-24-oate
acetic acid
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
methyl 3α-acetoxy-5β-chol-9(11)-en-24-oate
A
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
methyl 3α-acetoxy-5β-chol-11-ene-24-oate
water
sodium acetate
acetone
N-bromoacetamide
B
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
Conditions | Yield |
---|---|
Chromatographieren des Reaktionsprodukts an alkalihaltigem Aluminiumoxid; |
methyl 3α-acetoxy-5β-chol-11-ene-24-oate
water
acetone
N-bromoacetamide
A
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
B
methyl 3α-acetoxy-11-oxo-5β-cholan-24-oate
Conditions | Yield |
---|---|
Reaktion ueber mehrere Stufen; |
methyl 3α-acetoxy-5β-chol-11-ene-24-oate
water
tert-butyl alcohol
N-bromoacetamide
A
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
B
methyl 3α-acetoxy-11-oxo-5β-cholan-24-oate
Conditions | Yield |
---|---|
Reaktion ueber mehrere Stufen; |
9(11),(5β)-cholenic acid-3α-ol-12-one
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: diazomethane; diethyl ether 2: pyridine View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: acetic acid 2: hydrogen bromide; acetic acid; bromine 3: diazomethane; diethyl ether 4: pyridine View Scheme |
3α-hydroxy-12-oxo-5β-cholan-24-oic acid methyl ester
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: benzene; pyridine 2: bromine; acetic acid / Erwaermen des Reaktionsprodukts mit aethanol. Natriumaethylat 3: diazomethane; diethyl ether 4: pyridine View Scheme |
3α-acetoxy-12-oxo-5β-cholanoic acid-(24)
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: hydrogen bromide; acetic acid; bromine 2: diazomethane; diethyl ether 3: pyridine View Scheme | |
Multi-step reaction with 3 steps 1: bromine; acetic acid / Erwaermen des Reaktionsprodukts mit aethanol. Natriumaethylat 2: diazomethane; diethyl ether 3: pyridine View Scheme |
3α-acetoxy-11β-bromo-12α-hydroxy-5β-cholan-24-oic acid methyl ester
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: silver acetate; acetic acid 2: chromium (VI)-oxide; acetic acid View Scheme | |
Multi-step reaction with 2 steps 1: chromium (VI)-oxide; acetic acid 2: pyridine View Scheme |
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: diazomethane; diethyl ether 2: pyridine View Scheme |
3α-benzoyloxy-12-oxo-5β-cholanoic acid-(24)-methyl ester
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: bromine; acetic acid / Erwaermen des Reaktionsprodukts mit aethanol. Natriumaethylat 2: diazomethane; diethyl ether 3: pyridine View Scheme |
12α-chloro-3α-acetoxy-5β-cholen-(9(11))-oic acid-(24)-methyl ester
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: silver carbonate; aqueous acetone 2: chromium (VI)-oxide; acetic acid View Scheme |
12α-methoxy-3α-acetoxy-5β-cholen-(9(11))-oic acid-(24)-methyl ester
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: chloroform; hydrogen chloride 2: silver carbonate; aqueous acetone 3: chromium (VI)-oxide; acetic acid View Scheme |
9-alpha-hydroxyandrost-4-ene-3,17-dione
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: hydrogen / palladium 10% on activated carbon / N,N-dimethyl-formamide / 3 h / 25 - 35 °C / 3102.97 Torr 2.1: sulfuric acid / dichloromethane / 2.15 h / 10 - 35 °C 3.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 2 h / -45 - -40 °C / Inert atmosphere 4.1: potassium tert-butylate / tetrahydrofuran / 1.33 h / 25 - 35 °C / Inert atmosphere 4.2: 3 - 5 h / 25 - 35 °C / Inert atmosphere 4.3: Cooling 5.1: triethylamine / dmap / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 6.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 6.2: Cooling 7.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 8.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 7 h / 0 - 5 °C 9.1: potassium carbonate; hydrogen / palladium on activated charcoal / dichloromethane / 24 h / 20 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: hydrogen / palladium 10% on activated carbon / N,N-dimethyl-formamide / 3 h / 25 - 35 °C / 3102.97 Torr 2.1: sulfuric acid / dichloromethane / 2.15 h / 10 - 35 °C 3.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 2 h / -45 - -40 °C / Inert atmosphere 4.1: potassium tert-butylate / tetrahydrofuran / 1.33 h / 25 - 35 °C / Inert atmosphere 4.2: 3 - 5 h / 25 - 35 °C / Inert atmosphere 4.3: Cooling 5.1: triethylamine / dmap / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 6.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 6.2: Cooling 7.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 8.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 7 h / 0 - 5 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: hydrogen / palladium 10% on activated carbon / N,N-dimethyl-formamide / 3 h / 25 - 35 °C / 3102.97 Torr 2.1: sulfuric acid / dichloromethane / 2.15 h / 10 - 35 °C 3.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 2 h / -45 - -40 °C / Inert atmosphere 4.1: potassium tert-butylate / tetrahydrofuran / 1.33 h / 25 - 35 °C / Inert atmosphere 4.2: 3 - 5 h / 25 - 35 °C / Inert atmosphere 4.3: Cooling 5.1: triethylamine / dmap / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 6.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 6.2: Cooling 7.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 8.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 8 - 10 h / 0 °C 8.2: 2 h / 50 - 55 °C 8.3: 6 - 8 h / 25 - 30 °C View Scheme |
9α-hydroxy-5β-androstan-3,17-dione
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: sulfuric acid / dichloromethane / 2.15 h / 10 - 35 °C 2.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 2 h / -45 - -40 °C / Inert atmosphere 3.1: potassium tert-butylate / tetrahydrofuran / 1.33 h / 25 - 35 °C / Inert atmosphere 3.2: 3 - 5 h / 25 - 35 °C / Inert atmosphere 3.3: Cooling 4.1: triethylamine / dmap / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 5.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 5.2: Cooling 6.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 7.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 7 h / 0 - 5 °C 8.1: potassium carbonate; hydrogen / palladium on activated charcoal / dichloromethane / 24 h / 20 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: sulfuric acid / dichloromethane / 2.15 h / 10 - 35 °C 2.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 2 h / -45 - -40 °C / Inert atmosphere 3.1: potassium tert-butylate / tetrahydrofuran / 1.33 h / 25 - 35 °C / Inert atmosphere 3.2: 3 - 5 h / 25 - 35 °C / Inert atmosphere 3.3: Cooling 4.1: triethylamine / dmap / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 5.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 5.2: Cooling 6.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 7.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 7 h / 0 - 5 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: sulfuric acid / dichloromethane / 2.15 h / 10 - 35 °C 2.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 2 h / -45 - -40 °C / Inert atmosphere 3.1: potassium tert-butylate / tetrahydrofuran / 1.33 h / 25 - 35 °C / Inert atmosphere 3.2: 3 - 5 h / 25 - 35 °C / Inert atmosphere 3.3: Cooling 4.1: triethylamine / dmap / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 5.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 5.2: Cooling 6.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 7.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 8 - 10 h / 0 °C 7.2: 2 h / 50 - 55 °C 7.3: 6 - 8 h / 25 - 30 °C View Scheme |
(5β)-androst-9(11)-ene-3,17-dione
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 2 h / -45 - -40 °C / Inert atmosphere 2.1: potassium tert-butylate / tetrahydrofuran / 1.33 h / 25 - 35 °C / Inert atmosphere 2.2: 3 - 5 h / 25 - 35 °C / Inert atmosphere 2.3: Cooling 3.1: triethylamine / dmap / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 4.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 4.2: Cooling 5.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 6.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 7 h / 0 - 5 °C 7.1: potassium carbonate; hydrogen / palladium on activated charcoal / dichloromethane / 24 h / 20 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 2 h / -45 - -40 °C / Inert atmosphere 2.1: potassium tert-butylate / tetrahydrofuran / 1.33 h / 25 - 35 °C / Inert atmosphere 2.2: 3 - 5 h / 25 - 35 °C / Inert atmosphere 2.3: Cooling 3.1: triethylamine / dmap / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 4.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 4.2: Cooling 5.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 6.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 7 h / 0 - 5 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 2 h / -45 - -40 °C / Inert atmosphere 2.1: potassium tert-butylate / tetrahydrofuran / 1.33 h / 25 - 35 °C / Inert atmosphere 2.2: 3 - 5 h / 25 - 35 °C / Inert atmosphere 2.3: Cooling 3.1: triethylamine / dmap / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 4.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 4.2: Cooling 5.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 6.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 8 - 10 h / 0 °C 6.2: 2 h / 50 - 55 °C 6.3: 6 - 8 h / 25 - 30 °C View Scheme |
3α-hydroxy-5β-androst-9(11)-en-17-one
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: potassium tert-butylate / tetrahydrofuran / 1.33 h / 25 - 35 °C / Inert atmosphere 1.2: 3 - 5 h / 25 - 35 °C / Inert atmosphere 1.3: Cooling 2.1: triethylamine / dmap / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 3.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 3.2: Cooling 4.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 5.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 7 h / 0 - 5 °C 6.1: potassium carbonate; hydrogen / palladium on activated charcoal / dichloromethane / 24 h / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: potassium tert-butylate / tetrahydrofuran / 1.33 h / 25 - 35 °C / Inert atmosphere 1.2: 3 - 5 h / 25 - 35 °C / Inert atmosphere 1.3: Cooling 2.1: triethylamine / dmap / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 3.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 3.2: Cooling 4.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 5.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 7 h / 0 - 5 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: potassium tert-butylate / tetrahydrofuran / 1.33 h / 25 - 35 °C / Inert atmosphere 1.2: 3 - 5 h / 25 - 35 °C / Inert atmosphere 1.3: Cooling 2.1: triethylamine / dmap / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 3.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 3.2: Cooling 4.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 5.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 8 - 10 h / 0 °C 5.2: 2 h / 50 - 55 °C 5.3: 6 - 8 h / 25 - 30 °C View Scheme |
(Z)-3α-hydroxy-5β-pregna-9(11),17(20)-diene
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: triethylamine / dmap / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 2.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 2.2: Cooling 3.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 4.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 7 h / 0 - 5 °C 5.1: potassium carbonate; hydrogen / palladium on activated charcoal / dichloromethane / 24 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: triethylamine / dmap / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 2.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 2.2: Cooling 3.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 4.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 7 h / 0 - 5 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: triethylamine / dmap / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 2.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 2.2: Cooling 3.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 4.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 8 - 10 h / 0 °C 4.2: 2 h / 50 - 55 °C 4.3: 6 - 8 h / 25 - 30 °C View Scheme |
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
methyl 3α-acetoxy-12-oxo-5β-cholan-24-oate
Conditions | Yield |
---|---|
Stage #1: methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate With hydrogen; palladium 10% on activated carbon In ethyl acetate at 45 - 50℃; for 18h; Stage #2: With pyridinium chlorochromate In ethyl acetate at 20℃; for 2h; Stage #3: With hydrogen; palladium on activated charcoal In ethyl acetate at 45 - 50℃; under 2585.81 Torr; for 18h; | 95% |
With hydrogen; palladium 10% on activated carbon In ethyl acetate at 45 - 50℃; under 2585.81 Torr; for 16h; Product distribution / selectivity; | 83.1% |
Stage #1: methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate With hydrogen; palladium-on-charcoal In ethyl acetate at 45 - 50℃; under 2585.81 Torr; for 16h; Autoclave; Stage #2: With pyridinium chlorochromate In ethyl acetate at 25 - 35℃; for 2h; Product distribution / selectivity; | 83.1% |
Stage #1: methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate With palladium 10% on activated carbon; hydrogen In ethyl acetate at 45 - 50℃; under 2585.81 Torr; for 16h; Stage #2: With pyridinium chlorochromate In ethyl acetate at 25 - 35℃; for 2h; Concentration; Reagent/catalyst; Temperature; | 83.1% |
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 50℃; under 2585.81 Torr; for 16h; Autoclave; | 80% |
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
5β-chol-9(11)-en-3α,24-diol
Conditions | Yield |
---|---|
With aluminum (III) chloride; lithium aluminium tetrahydride In tetrahydrofuran for 4h; Reflux; | 64% |
With lithium aluminium tetrahydride; aluminium trichloride |
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
3α-hydroxy-5β-chol-9(11)-en-24-oic acid
Conditions | Yield |
---|---|
With sodium ethanolate; hydrazine hydrate at 170℃; |
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
9(11),(5β)-cholenic acid-3α-ol-12-one
Conditions | Yield |
---|---|
With potassium hydroxide | |
Multi-step reaction with 2 steps 1: hydrogen chloride; methanol 2: methanol. KOH-solution View Scheme |
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
methyl 3α-hydroxy-12-oxo-5β-chol-9(11)-en-24-oate
Conditions | Yield |
---|---|
With hydrogenchloride; methanol | |
With methanol; potassium hydroxide at 20℃; for 1.5h; |
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
A
12β-hydroxy-3α-acetoxy-5β-cholen-(9(11))-oic acid-(24)-methyl ester
B
12α-hydroxy-3α-acetoxy-5β-cholen-(9(11))-oic acid-(24)-methyl ester
Conditions | Yield |
---|---|
With ethanol; acetic acid; platinum Hydrogenation; |
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
methyl 3α-acetoxy-12-hydroxy-9(11)-cholenate
Conditions | Yield |
---|---|
With sodium tetrahydroborate; cerium(III) chloride In methanol for 0.5h; Ambient temperature; | 1.28 g |
ethanol
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
acetic acid
methyl 3α-acetoxy-5β-chol-9(11)-en-24-oate
Conditions | Yield |
---|---|
Hydrogenation; |
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
sodium ethanolate
hydrazine hydrate
A
methyl 3α-acetoxy-5β-chol-9(11)-en-24-oate
B
methyl 3α-acetoxy-5β-chol-11-ene-24-oate
Conditions | Yield |
---|---|
at 170℃; Behandeln des Reaktionsprodukts mit Diazomethan in Aether und Behandeln des danach isolierten Reaktionsprodukts mit Acetanhydrid und Pyridin; |
ethanol
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
acetic acid
A
12β-hydroxy-3α-acetoxy-5β-cholen-(9(11))-oic acid-(24)-methyl ester
B
12α-hydroxy-3α-acetoxy-5β-cholen-(9(11))-oic acid-(24)-methyl ester
Conditions | Yield |
---|---|
Hydrogenation; |
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
methyl 3α,12β-diacetoxy-9(11)-cholenate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.28 g / NaBH4, CeCl3*6H2O / methanol / 0.5 h / Ambient temperature 2: toluene; pyridine / 6 h / 100 °C View Scheme |
methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate
methyl 3α,12α-diacetoxy-9(11)-cholenate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.28 g / NaBH4, CeCl3*6H2O / methanol / 0.5 h / Ambient temperature 2: toluene; pyridine / 6 h / 100 °C View Scheme |
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