Methyl 3alpha,12alpha-diacetyloxy-7-oxo-5beta-cholanate

Base Information

• Chemical Name: Methyl 3alpha,12alpha-diacetyloxy-7-oxo-5beta-cholanate
• CAS No.: 21066-20-6
• Molecular Formula: C29H44O7
• Molecular Weight: 504.664
• UNII: AW92R2931N
• Nikkaji Number: J22.727G
• Wikidata: Q27274149
• Mol file: 21066-20-6.mol

Synonyms:21066-20-6;Methyl 3alpha,12alpha-diacetyloxy-7-oxo-5beta-cholanate;AW92R2931N;UNII-AW92R2931N;5beta-Cholanic acid, 3alpha,12alpha-dihydroxy-7-oxo-, methyl ester, diacetate;5beta-Cholanic acid, 3alpha,12alpha-dihydroxy-7-oxo-, methyl ester, diacetate, (+)-;Cholan-24-oic acid, 3,12-bis(acetyloxy)-7-oxo-, methyl ester, (3alpha,5beta,12alpha)-;Cholan-24-oic acid, 3,12-bis(acetyloxy)-7-oxo-, methyl ester, (3.alpha.,5.beta.,12.alpha.)-;methyl (4R)-4-[(3R,5S,8R,9S,10S,12S,13R,14S,17R)-3,12-diacetyloxy-10,13-dimethyl-7-oxo-1,2,3,4,5,6,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoate;SCHEMBL21658651;DATLSYWCILADOV-YQLBWAHWSA-;DATLSYWCILADOV-YQLBWAHWSA-N;Methyl 3,12-bis(acetyloxy)-7-oxocholan-24-oate #;Q27274149;METHYL 3.ALPHA.,12.ALPHA.-DIACETYLOXY-7-OXO-5.BETA.-CHOLANATE;5.BETA.-CHOLANIC ACID, 3.ALPHA.,12.ALPHA.-DIHYDROXY-7-OXO-, METHYL ESTER, DIACETATE;5.BETA.-CHOLANIC ACID, 3.ALPHA.,12.ALPHA.-DIHYDROXY-7-OXO-, METHYL ESTER, DIACETATE, (+)-;InChI=1/C29H44O7/c1-16(7-10-26(33)34-6)21-8-9-22-27-23(15-25(29(21,22)5)36-18(3)31)28(4)12-11-20(35-17(2)30)13-19(28)14-24(27)32/h16,19-23,25,27H,7-15H2,1-6H3/t16-,19+,20-,21-,22+,23+,25+,27+,28+,29-/m1/s1

Chemical Property of Methyl 3alpha,12alpha-diacetyloxy-7-oxo-5beta-cholanate

Chemical Property:

• PSA: 95.97000
• Density: 1.14
• LogP: 4.88690
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 504.30870374
• Heavy Atom Count: 36
• Complexity: 898

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(C(CC3C2C(=O)CC4C3(CCC(C4)OC(=O)C)C)OC(=O)C)C
• Isomeric SMILES: C[C@H](CCC(=O)OC)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2C(=O)C[C@H]4[C@@]3(CC[C@H](C4)OC(=O)C)C)OC(=O)C)C

Technology Process of Methyl 3alpha,12alpha-diacetyloxy-7-oxo-5beta-cholanate

There total 10 articles about Methyl 3alpha,12alpha-diacetyloxy-7-oxo-5beta-cholanate 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: 94.0%

methyl 3α-acetyloxy-7-oxo-12α-hydroxy-5β-cholan-24-oate (21059-39-2) + acetic anhydride (108-24-7) → methyl 7-dehydrocholate diacetate (methyl 3α,12α-diacetoxy-7-oxo-5β-cholan-24-oate) (21066-20-6)

Guidance literature:

With dmap; triethylamine; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/jo0606453

Reference yield: 90.0%

methyl 3α,12α-dihydroxy-7-oxo-5β-cholate (15073-97-9,15180-34-4,81644-39-5,81644-40-8,10538-65-5) + acetic anhydride (108-24-7) → methyl 7-dehydrocholate diacetate (methyl 3α,12α-diacetoxy-7-oxo-5β-cholan-24-oate) (21066-20-6)

Guidance literature:

With dmap; triethylamine; for 24h; Ambient temperature;

DOI:10.1039/c39930001469

Reference yield:

7-ketodeoxycholic acid (911-40-0) → methyl 7-dehydrocholate diacetate (methyl 3α,12α-diacetoxy-7-oxo-5β-cholan-24-oate) (21066-20-6)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / Reflux

2: pyridine / dmap / dichloromethane / 12 h / 20 °C

With pyridine; hydrogenchloride; dmap; In dichloromethane;

upstream raw materials:

methyl 3α,12α-dihydroxy-7-oxo-5β-cholate

acetic anhydride

methyl 3α-acetyloxy-7-oxo-12α-hydroxy-5β-cholan-24-oate

methyl cholate 3-acetate

Downstream raw materials:

Biphenyl-4-carboxylic acid (3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-12-acetoxy-3-hydroxy-17-((R)-3-methoxycarbonyl-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-7-yl ester

Biphenyl-4-carboxylic acid (3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,12-diacetoxy-17-((R)-3-methoxycarbonyl-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-7-yl ester

Biphenyl-4-carboxylic acid (3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-12-acetoxy-3-acryloyloxy-17-((R)-3-methoxycarbonyl-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-7-yl ester

methyl 12α-acetoxy-3α,6α-dihydroxy-7-oxo-5β-cholanoate