(5beta,7alpha,12alpha)-7,12-Bis(acetyloxy)-3-oxocholan-24-oic acid

Base Information

• Chemical Name: (5beta,7alpha,12alpha)-7,12-Bis(acetyloxy)-3-oxocholan-24-oic acid
• CAS No.: 300386-87-2
• Molecular Formula: C28H42O7
• Molecular Weight: 490.637
• Mol file: 300386-87-2.mol

Synonyms:3-Oxo-7a,12a-diformyloxy-5b-cholanic acid;3-oxo-7Alpha,12Alpha-diformyloxy-5Beta-cholan-24-oic acid;(5beta,7alpha,12alpha)-7,12-Bis(acetyloxy)-3-oxocholan-24-oic acid;

Chemical Property of (5beta,7alpha,12alpha)-7,12-Bis(acetyloxy)-3-oxocholan-24-oic acid

Chemical Property:

• PSA: 106.97000
• Density: 1.18
• LogP: 4.79850
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

3-OXO-7ALPHA,12ALPHA-DIFORMYLOXY-5BETA-CHOLANIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (5beta,7alpha,12alpha)-7,12-Bis(acetyloxy)-3-oxocholan-24-oic acid

There total 8 articles about (5beta,7alpha,12alpha)-7,12-Bis(acetyloxy)-3-oxocholan-24-oic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

methyl 3-keto-7,12-diacetylcholate (4947-65-3) → 3-oxo-7α,12α-diacetoxy-5β-cholan-24-oic acid (300386-87-2)

Guidance literature:

With sodium hydroxide; In isopropyl alcohol; at 80 ℃;

DOI:10.1021/jm000952f

Reference yield:

methyl cholate (1448-36-8) → 3-oxo-7α,12α-diacetoxy-5β-cholan-24-oic acid (300386-87-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / TMSOTf / CH₂Cl₂ / 0.08 h / 20 °C

2: 96 percent / K₂CO₃; MeOH / 2 h / 20 °C

3: 81 percent / CrO₃; aq. H₂SO₄ / acetone

4: 93 percent / aq. NaOH / propan-2-ol / 80 °C

With chromium(VI) oxide; methanol; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; potassium carbonate; In dichloromethane; isopropyl alcohol; acetone; 3: Jones oxidation;

DOI:10.1021/jm000952f

Reference yield:

methyl 3,7,12-triacetoxycholan-24-oate (6818-44-6) → 3-oxo-7α,12α-diacetoxy-5β-cholan-24-oic acid (300386-87-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / K₂CO₃; MeOH / 2 h / 20 °C

2: 81 percent / CrO₃; aq. H₂SO₄ / acetone

3: 93 percent / aq. NaOH / propan-2-ol / 80 °C

With chromium(VI) oxide; methanol; sodium hydroxide; sulfuric acid; potassium carbonate; In isopropyl alcohol; acetone; 2: Jones oxidation;

DOI:10.1021/jm000952f

upstream raw materials:

3α-hydroxy-7α,12α-diacetoxy-5β-cholan-24-oic acid

7α,12α-dihydroxy-3-oxocholanoic acid

acetic anhydride

methyl 3-keto-7,12-diacetylcholate

Downstream raw materials:

3-oxo-12α-hydroxy-4,6-choladien-24-oic acid

Refernces