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4472-02-0

Basic Information
CAS No.: 4472-02-0
Name: 3α-Acetyloxy-12-oxo-5β-chol-9(11)-en-24-oic acid methyl ester
Article Data: 21
Molecular Structure:
Molecular Structure of 4472-02-0 (3α-Acetyloxy-12-oxo-5β-chol-9(11)-en-24-oic acid methyl ester)
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
Synthetic route
5143-55-5

methyl 3α-acetoxy-12-oxo-5β-cholan-24-oate

4472-02-0

methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate

Conditions
ConditionsYield
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;
30365-63-0

methyl 3α-acetoxy-5β-chol-9(11)-en-24-oate

A

1311972-67-4

C31H50O6

B

4472-02-0

methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate

Conditions
ConditionsYield
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%
30365-63-0

methyl 3α-acetoxy-5β-chol-9(11)-en-24-oate

4472-02-0

methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate

Conditions
ConditionsYield
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℃;
1311972-67-4

C31H50O6

4472-02-0

methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate

Conditions
ConditionsYield
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.
110-86-1

pyridine

88128-14-7

3α-acetoxy-11β-bromo-12-oxo-5β-cholan-24-oic acid methyl ester

4472-02-0

methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate

108-75-8

2,4,6-trimethyl-pyridine

17550-22-0

3α-acetoxy-11α-bromo-12-oxo-5β-cholan-24-oic acid methyl ester

4472-02-0

methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate

30365-63-0

methyl 3α-acetoxy-5β-chol-9(11)-en-24-oate

A

4472-02-0

methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate

B

107329-63-5

3α-acetoxy-9,11β-epoxy-5β,9β-cholan-24-oic acid methyl ester

Conditions
ConditionsYield
With potassium permanganate; acetic acid
24637-48-7

12α-hydroxy-3α-acetoxy-5β-cholen-(9(11))-oic acid-(24)-methyl ester

4472-02-0

methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate

Conditions
ConditionsYield
With chromium(VI) oxide; acetic acid
88128-14-7

3α-acetoxy-11β-bromo-12-oxo-5β-cholan-24-oic acid methyl ester

4472-02-0

methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate

Conditions
ConditionsYield
With pyridine
65065-56-7

methyl 3α-hydroxy-12-oxo-5β-chol-9(11)-en-24-oate

108-24-7

acetic anhydride

4472-02-0

methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate

Conditions
ConditionsYield
With pyridine
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