methyl 3α,12α-diacetoxy-6α,7α-epoxy-5β-cholanoate

Base Information

• Chemical Name: methyl 3α,12α-diacetoxy-6α,7α-epoxy-5β-cholanoate
• CAS No.: 133181-58-5
• Molecular Formula: C₂₉H₄₄O₇
• Molecular Weight: 504.664

Synonyms:methyl 3α,12α-diacetoxy-6α,7α-epoxy-5β-cholanoate

Chemical Property of methyl 3α,12α-diacetoxy-6α,7α-epoxy-5β-cholanoate

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Technology Process of methyl 3α,12α-diacetoxy-6α,7α-epoxy-5β-cholanoate

There total 1 articles about methyl 3α,12α-diacetoxy-6α,7α-epoxy-5β-cholanoate 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:

7-ketodeoxycholic acid (911-40-0) → methyl 3α,12α-diacetoxy-6α,7α-epoxy-5β-cholanoate (133181-58-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: hydrogenchloride / Reflux

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

3.1: bromine; acetic acid / 48 h / 20 °C

4.1: zinc(II) tetrahydroborate / benzene; diethyl ether / 22 h / 20 °C

4.2: 1 h / Reflux

5.1: 2,6-di-tert-butyl-4-methyl-phenol; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / Reflux

With pyridine; hydrogenchloride; zinc(II) tetrahydroborate; 2,6-di-tert-butyl-4-methyl-phenol; bromine; acetic acid; 3-chloro-benzenecarboperoxoic acid; dmap; In diethyl ether; dichloromethane; benzene;

Reference yield:

methyl 3α,12α-diacetoxy-6α,7α-epoxy-5β-cholanoate (133181-58-5) → 3α,6β,7α,12α-tetrahydroxy-5β-cholan-24-oic acid (80875-93-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) BF₃*Et₂O, 2.) water / 1.) DMF, RT, overnight

2: 84 percent / KOH / methanol / 10 h / Heating

With potassium hydroxide; boron trifluoride diethyl etherate; water; In methanol;

DOI:10.1016/0039-128X(90)90048-G

Reference yield:

(R)-4-((3R,5R,8R,9S,10R,12S,13R,14S,17R)-3,12-Diacetoxy-10,13-dimethyl-hexadecahydro-20-oxa-cyclopropa[6,7]cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester (133181-58-5) → 3α,6β,7α,12α-tetrahydroxy-5β-cholan-24-oic acid (80875-93-0)

Guidance literature:

With 1.) acid, 2.) alkali; Multistep reaction; by two step hydrolysis;

DOI:10.1248/cpb.37.557

upstream raw materials:

7-ketodeoxycholic acid

Downstream raw materials:

3α,6β,7α,12α-tetrahydroxy-5β-cholan-24-oic acid

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