3-Oxo-7α-hydroxy-5α-cholanic acid methyl ester

Base Information

• Chemical Name: 3-Oxo-7α-hydroxy-5α-cholanic acid methyl ester
• CAS No.: 14772-96-4
• Molecular Formula: C25H40O4
• Molecular Weight: 404.59
• Mol file: 14772-96-4.mol

Synonyms:3-Oxo-7α-hydroxy-5α-cholan-24-oic acid methyl ester;3-Oxo-7α-hydroxy-5α-cholanic acid methyl ester;7α-Hydroxy-3-oxo-5α-cholan-24-oic acid methyl ester

Chemical Property of 3-Oxo-7α-hydroxy-5α-cholanic acid methyl ester

Chemical Property:

• Melting Point: 137 - 139 °C (H2O)
• PSA: 63.60000
• LogP: 4.77450

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Oxo-7α-hydroxy-5α-cholanic acid methyl ester

There total 7 articles about 3-Oxo-7α-hydroxy-5α-cholanic acid methyl ester 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: 12.0%

(R)-4-((7R,8S,9S,10R,13R,14S,17R)-7-Hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester (125626-78-0) → methyl (5β,7α)-12-hydroxy-3-oxo-cholan-24-oate (14773-00-3) + methyl 3-oxo-7α-hydroxy-5α-cholan-24-oate (14772-96-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 4h; under 735.5 Torr; Ambient temperature;

DOI:10.1016/0039-128X(89)90022-6

Reference yield:

methyl (5β,7α)-12-hydroxy-3-oxo-cholan-24-oate (14773-00-3) → methyl 3-oxo-7α-hydroxy-5α-cholan-24-oate (14772-96-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 22 percent / DDQ / dioxane / 4 h / Heating

2: 12 percent / H₂ / Pd-C / ethyl acetate / 4 h / 735.5 Torr / Ambient temperature

With hydrogen; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In 1,4-dioxane; ethyl acetate;

DOI:10.1016/0039-128X(89)90022-6

Reference yield:

→ 7α-Hydroxy-3-keto-5β-cholansaeure-methylester (14772-96-4,14773-00-3,67371-28-2,132089-90-8)

Guidance literature:

7α-Acetoxy-3-keto-5β-cholansaeure-methylester, 1. wss.-methanol. KOH, Sieden, 2. Methylierung;

upstream raw materials:

(R)-4-((7R,8S,9S,10R,13R,14S,17R)-7-Hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester

methyl (5β,7α)-12-hydroxy-3-oxo-cholan-24-oate

Downstream raw materials:

chenodeoxycholic acid

(5α,7α,24R)-7,24-dihydroxy-3-ketocholestane

3α,7α-dihydroxy-5α-cholanoic acid methyl ester

Refernces

• 1、 Tserng. "A convenient synthesis of 3-keto bile acids by selective oxidation of bile acids with silver carbonate-Celite". . p. 501 - 504. Retrieved 2007/10/14.