5beta-Cholanic acid 3,7-dione methyl ester

Base Information

• Chemical Name: 5beta-Cholanic acid 3,7-dione methyl ester
• CAS No.: 7753-72-2
• Molecular Formula: C25H38 O4
• Molecular Weight: 402.574
• DSSTox Substance ID: DTXSID70557798
• Nikkaji Number: J596.078I
• Wikidata: Q82439820
• Mol file: 7753-72-2.mol

Synonyms:5beta-Cholanic acid 3,7-dione methyl ester;7753-72-2;5|A-Cholanic acid 3,7-dione methyl ester;SCHEMBL3219278;DTXSID70557798;MFCD00271381;HY-W127586;methyl (4R)-4-[(5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7-dioxo-2,4,5,6,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate;Methyl (5beta)-3,7-dioxocholan-24-oate;CS-0185807;5beta-Cholanic acid 3,7-dione methyl ester, >=98%

Chemical Property of 5beta-Cholanic acid 3,7-dione methyl ester

Chemical Property:

• PSA: 60.44000
• LogP: 4.98270
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 402.27700969
• Heavy Atom Count: 29
• Complexity: 699

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)OC)C1CCC2C1(CCC3C2C(=O)CC4C3(CCC(=O)C4)C)C
• Isomeric SMILES: C[C@H](CCC(=O)OC)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C(=O)C[C@H]4[C@@]3(CCC(=O)C4)C)C

Technology Process of 5beta-Cholanic acid 3,7-dione methyl ester

There total 8 articles about 5beta-Cholanic acid 3,7-dione 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: 62.0%

chenodeoxycholic acid methyl ester (3057-04-3) → 7-ketolithocholic methyl ester (10538-59-7) + methyl 3,7-dioxocholan-24-oate (7753-72-2)

Guidance literature:

With silica gel; pyridinium chlorochromate; In chloroform; at 20 ℃; for 5h; Inert atmosphere;

Reference yield: 36.0%

chenodeoxycholic acid methyl ester (3057-04-3) → methyl (5β,7α)-12-hydroxy-3-oxo-cholan-24-oate (14773-00-3) + 7-ketolithocholic methyl ester (10538-59-7) + methyl 3,7-dioxocholan-24-oate (7753-72-2)

Guidance literature:

With dimethoxydioxirane*H₂O; In acetone; at 0 - 5 ℃; for 16h;

DOI:10.1016/S0040-4039(99)00834-5

Reference yield:

chenodeoxycholic acid (474-25-9) → 7-ketolithocholic methyl ester (10538-59-7) + methyl 3,7-dioxocholan-24-oate (7753-72-2)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / 2 h / Reflux; Inert atmosphere

2: silica gel; pyridinium chlorochromate / chloroform / 5 h / 20 °C / Inert atmosphere

With silica gel; toluene-4-sulfonic acid; pyridinium chlorochromate; In chloroform;

upstream raw materials:

chenodeoxycholic acid methyl ester

chenodeoxycholic acid

Downstream raw materials:

ursodeoxycholic acid

7-ketolithocholic methyl ester

(R)-4-((3S,5S,8R,9S,10S,13R,14S,17R)-3-Hydroxy-10,13-dimethyl-7-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester

Refernces

• 1、 Buxton, P. Christopher,Marples, Brian A.,Toon, Richard C.,Waddington, Victoria L.. "Selective dimethyldioxirane oxidation of bile acid methyl esters". . p. 4729 - 4732. Retrieved 2007/10/03.