Methyl 3alpha-((ethoxycarbonyl)oxy)-12-oxo-5-beta-cholan-24-oate

Base Information

• Chemical Name: Methyl 3alpha-((ethoxycarbonyl)oxy)-12-oxo-5-beta-cholan-24-oate
• CAS No.: 83918-75-6
• Molecular Formula: C28H44 O6
• Molecular Weight: 476.654
• European Community (EC) Number: 281-311-0
• DSSTox Substance ID: DTXSID301004072
• Nikkaji Number: J332.894E
• Wikidata: Q82998879
• Mol file: 83918-75-6.mol

Synonyms:EINECS 281-311-0;83918-75-6;Methyl 3alpha-((ethoxycarbonyl)oxy)-12-oxo-5-beta-cholan-24-oate;Methyl 3alpha-[(ethoxycarbonyl)oxy]-12-oxo-5-beta-cholan-24-oate;DTXSID301004072;Methyl 3-[(ethoxycarbonyl)oxy]-12-oxocholan-24-oate;3alpha-[(Ethoxycarbonyl)oxy]-12-oxo-5beta-cholan-24-oic acid methyl ester

Chemical Property of Methyl 3alpha-((ethoxycarbonyl)oxy)-12-oxo-5-beta-cholan-24-oate

Chemical Property:

• PSA: 78.90000
• LogP: 5.95530
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 476.31378912
• Heavy Atom Count: 34
• Complexity: 794

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)OC1CCC2(C(C1)CCC3C2CC(=O)C4(C3CCC4C(C)CCC(=O)OC)C)C
• Isomeric SMILES: CCOC(=O)O[C@@H]1CC[C@]2([C@@H](C1)CC[C@@H]3[C@@H]2CC(=O)[C@]4([C@H]3CC[C@@H]4[C@H](C)CCC(=O)OC)C)C

Technology Process of Methyl 3alpha-((ethoxycarbonyl)oxy)-12-oxo-5-beta-cholan-24-oate

There total 5 articles about Methyl 3alpha-((ethoxycarbonyl)oxy)-12-oxo-5-beta-cholan-24-oate 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: 88.0%

methyl 3α-cathyloxy-12α-hydroxy-5β-cholan-24-oate (70779-09-8) → methyl 3α-cathyloxy-12-oxo-5β-cholan-24-oate (83918-75-6)

Guidance literature:

With jones reagent; In acetone; at 10 ℃; for 2h;

DOI:10.1080/00397910008087246

Reference yield:

methyl deoxycholate (3245-38-3) → methyl 3α-cathyloxy-12-oxo-5β-cholan-24-oate (83918-75-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

2: 88 percent / Jones reagent / acetone / 2 h / 10 °C

With pyridine; jones reagent; In dichloromethane; acetone; 1: Acylation / 2: Oxidation;

DOI:10.1080/00397910008087246

Reference yield:

Deoxycholic acid (83-44-3) → methyl 3α-cathyloxy-12-oxo-5β-cholan-24-oate (83918-75-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / acetyl chloride / 2 h / Ambient temperature

2: 86 percent / pyridine / 1 h / 0 °C

3: 85 percent / Jones' reagent / acetone / 0.17 h / Ambient temperature

With pyridine; jones' reagent; acetyl chloride; In acetone;

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

upstream raw materials:

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

methyl deoxycholate

Deoxycholic acid

Downstream raw materials:

12-oxolithocholic acid

Refernces

• 1、 Gao, Hongwu,Dias, Jerry Ray. "Cyclocholates with 12-Oxo and 7,12-Oxo Groups". . p. 719 - 724. Retrieved 2007/10/03.