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

Base Information

• Chemical Name: Methyl 3alpha,7alpha-diacetoxy-12-oxo-5beta-cholanate
• CAS No.: 28535-81-1
• Molecular Formula: C29H44 O7
• Molecular Weight: 504.664
• European Community (EC) Number: 249-070-6
• UNII: 61WHO74ZK2
• DSSTox Substance ID: DTXSID80951223
• Nikkaji Number: J130.604I
• Wikidata: Q27263387
• ChEMBL ID: CHEMBL3618378
• Mol file: 28535-81-1.mol

Synonyms:28535-81-1;Methyl 3alpha,7alpha-diacetoxy-12-oxo-5beta-cholanate;UNII-61WHO74ZK2;61WHO74ZK2;EINECS 249-070-6;Methyl 3alpha,7alpha-Diacetoxy-12-oxo-5beta-cholan-24-oate;Methyl 3-alpha,7-alpha-diacetoxy-12-oxo-5-beta-cholan-24-oate;EC 249-070-6;methyl (4R)-4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-diacetyloxy-10,13-dimethyl-12-oxo-1,2,3,4,5,6,7,8,9,11,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoate;CHEMBL3618378;SCHEMBL11099904;DTXSID80951223;Q27263387;3alpha,7alpha-Diacetoxy-12-ketocholanic acid methyl ester;Methyl 3alphalpha,7alpha-diacetoxy-12-oxo-5beta-cholan-24-oate;METHYL 3.ALPHA.,7.ALPHA.-DIACETOXY-12-OXO-5.BETA.-CHOLAN-24-OATE;METHYL 3.ALPHA.,7.ALPHA.-DIACETOXY-12-OXO-5.BETA.-CHOLANATE;5.BETA.-CHOLAN-24-OIC ACID, 3.ALPHA.,7.ALPHA.-DIHYDROXY-12-OXO-, METHYL ESTER, DIACETATE;Cholan-24-oic acid, 3,7-bis(acetyloxy)-12-oxo-, methyl ester, (3.alpha.,5.beta.,7.alpha.)-

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

Chemical Property:

• Melting Point: 177-179 °C
• Boiling Point: 559.2°Cat760mmHg
• Flash Point: 233.6°C
• PSA: 95.97000
• Density: 1.14g/cm³
• LogP: 4.88690
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), DMSO (Slightly)
• XLogP3: 4.7
• 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:

99.9% ^*data from raw suppliers

Methyl 3α,7α-Diacetoxy-12-oxo-5β-cholan-24-oate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)OC)C1CCC2C1(C(=O)CC3C2C(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(=O)C[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)OC(=O)C)C)OC(=O)C)C
• Uses: Methyl 3α,7α-Diacetoxy-12-oxo-5β-cholan-24-oate is an intermediate in the synthesis of 12β-Hydroxyisocholic Acid (H943480), a bile acid.

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

There total 11 articles about Methyl 3alpha,7alpha-diacetoxy-12-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: 98.0%

methyl 3α,7α-diacetoxy-12α-hydroxy cholanate (3749-87-9) → methyl 3α,7α-diacetoxy-12-one-5β-cholest-24-carboxylate (28535-81-1)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; water; In acetone; at 0 - 10 ℃; for 0.0833333h;

DOI:10.1021/jm051114u

Reference yield: 94.0%

methyl 3α-cathyloxy-12α-hydroxy-5β-cholan-24-oate (70779-09-8) → methyl 3α,7α-diacetoxy-12-one-5β-cholest-24-carboxylate (28535-81-1)

Guidance literature:

With potassium chromate; In acetic acid; for 15h; Ambient temperature;

DOI:10.1002/(SICI)1099-0690(199804)1998:4<719::AID-EJOC719>3.0.CO;2-F

Reference yield:

methyl cholate (1448-36-8) → methyl 3α,7α-diacetoxy-12-one-5β-cholest-24-carboxylate (28535-81-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / Et₃N; DMAP / CH₂Cl₂ / 5 h / 25 °C

2: 98 percent / CrO₃; H₂SO₄; H₂O / acetone / 0.08 h / 0 - 10 °C

With chromium(VI) oxide; dmap; sulfuric acid; water; triethylamine; In dichloromethane; acetone;

DOI:10.1021/jm051114u

upstream raw materials:

diazomethane

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

methyl 3α,7α-diacetoxy-12α-hydroxy cholanate

methyl 3α-cathyloxy-12α-hydroxy-5β-cholan-24-oate

Downstream raw materials:

7-Ketolithocholic acid

3α,7β-dihydroxy-5β-cholan-24-oic acid methyl ester

ursodeoxycholic acid

Methyl Chenodeoxycholate Diacetate