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CAS No.: | 4472-02-0 |
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Name: | 3α-Acetyloxy-12-oxo-5β-chol-9(11)-en-24-oic acid methyl ester |
Article Data: | 21 |
Molecular Structure: | |
Formula: | C27H40O5 |
Molecular Weight: | 444.612 |
Synonyms: | Methyl Ursodeoxycholate;methyl ester of ursodeoxycholic acid;Ursodeoxycholic Acid Methyl Ester;Methyl 3|A,7|A-Dihydroxy-5|A-cholanoate; |
Density: | 1.12g/cm3 |
Boiling Point: | 531°Cat760mmHg |
Flash Point: | 224.6°C |
PSA: | 69.67000 |
LogP: | 5.26540 |
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 |