Methyl 3alpha-((ethoxycarbonyl)oxy)-12alpha-hydroxy-7-oxo-5beta-cholan-24-oate

Base Information

• Chemical Name: Methyl 3alpha-((ethoxycarbonyl)oxy)-12alpha-hydroxy-7-oxo-5beta-cholan-24-oate
• CAS No.: 21059-40-5
• Molecular Formula: C28H44 O7
• Molecular Weight: 492.653
• European Community (EC) Number: 244-183-7
• DSSTox Substance ID: DTXSID60943368
• Mol file: 21059-40-5.mol

Synonyms:21059-40-5;Methyl 3alpha-((ethoxycarbonyl)oxy)-12alpha-hydroxy-7-oxo-5beta-cholan-24-oate;methyl 3-[(ethoxycarbonyl)oxy]-12-hydroxy-7-oxocholan-24-oate;DTXSID60943368;EINECS 244-183-7

Chemical Property of Methyl 3alpha-((ethoxycarbonyl)oxy)-12alpha-hydroxy-7-oxo-5beta-cholan-24-oate

Chemical Property:

• Boiling Point: 595.9°Cat760mmHg
• Flash Point: 188°C
• PSA: 99.13000
• Density: 1.16g/cm³
• LogP: 4.92610
• XLogP3: 5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 492.30870374
• Heavy Atom Count: 35
• Complexity: 826

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)OC1CCC2(C(C1)CC(=O)C3C2CC(C4(C3CCC4C(C)CCC(=O)OC)C)O)C

Technology Process of Methyl 3alpha-((ethoxycarbonyl)oxy)-12alpha-hydroxy-7-oxo-5beta-cholan-24-oate

There total 6 articles about Methyl 3alpha-((ethoxycarbonyl)oxy)-12alpha-hydroxy-7-oxo-5beta-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: 81.3%

3α-ethoxycarbonyloxy-7α,12α-dihydroxy-5β-cholan-24-oic acid methyl ester (21059-36-9) → methyl 3α-ethoxycarbonyloxy-12α-hydroxy-7-oxo-5β-cholanate (21059-40-5)

Guidance literature:

With acetic acid; N-bromoacetamide; In water; acetone; for 1h;

DOI:10.1135/cccc19952147

Reference yield:

methyl cholate (1448-36-8) → methyl 3α-ethoxycarbonyloxy-12α-hydroxy-7-oxo-5β-cholanate (21059-40-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / pyridine / 0 °C

2: 81.3 percent / N-bromoacetamide, AcOH / acetone; H₂O / 1 h

With acetic acid; N-bromoacetamide; In pyridine; water; acetone;

DOI:10.1135/cccc19952147

Reference yield:

3α-ethoxycarbonyloxy-7α,12α-dihydroxy-5β-cholan-24-oic acid methyl ester (21059-36-9) + N-bromoacetamide (79-15-2) → methyl 3α-ethoxycarbonyloxy-12α-hydroxy-7-oxo-5β-cholanate (21059-40-5)

Guidance literature:

DOI:10.1021/ja01180a016

upstream raw materials:

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

chloroformic acid ethyl ester

3α-ethoxycarbonyloxy-7α,12α-dihydroxy-5β-cholan-24-oic acid methyl ester

N-bromoacetamide

Downstream raw materials:

3α-ethoxycarbonyloxy-7,12-dioxo-5β-cholan-24-oic acid methyl ester