(8S,20R)-des-A,B-8-benzoyloxy-20-[4'-hydroxy-4'-methylpent-(1'E)-en-yl]-pregnane

Base Information

Chemical Name:(8S,20R)-des-A,B-8-benzoyloxy-20-[4'-hydroxy-4'-methylpent-(1'E)-en-yl]-pregnane
CAS No.:1588410-77-8
Molecular Formula:C₂₅H₃₆O₃
Molecular Weight:384.559
Hs Code.:

Synonyms:(8S,20R)-des-A,B-8-benzoyloxy-20-[4'-hydroxy-4'-methylpent-(1'E)-en-yl]-pregnane

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Chemical Property of (8S,20R)-des-A,B-8-benzoyloxy-20-[4'-hydroxy-4'-methylpent-(1'E)-en-yl]-pregnane

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Technology Process of (8S,20R)-des-A,B-8-benzoyloxy-20-[4'-hydroxy-4'-methylpent-(1'E)-en-yl]-pregnane

There total 1 articles about (8S,20R)-des-A,B-8-benzoyloxy-20-[4'-hydroxy-4'-methylpent-(1'E)-en-yl]-pregnane 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: 47.0%

: 66774-71-8
Benzoic acid (1R,3aR,4S,7aR)-7a-methyl-1-((S)-1-methyl-2-oxo-ethyl)-octahydro-inden-4-yl ester

: 67883-18-5
(3-Hydroxy-3-methylbutyl)triphenylphosphoniumbromid

: 1588410-77-8
(8S,20R)-des-A,B-8-benzoyloxy-20-[4'-hydroxy-4'-methylpent-(1'E)-en-yl]-pregnane

Guidance literature:: (3-Hydroxy-3-methylbutyl)triphenylphosphoniumbromid; With n-butyllithium; In tetrahydrofuran; at -20 ℃; for 1h;

Benzoic acid (1R,3aR,4S,7aR)-7a-methyl-1-((S)-1-methyl-2-oxo-ethyl)-octahydro-inden-4-yl ester; In tetrahydrofuran; at -20 - 20 ℃; for 22h; diastereoselective reaction;
DOI:10.1016/j.steroids.2014.01.012

Reference yield: 96.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 1588410-77-8
(8S,20R)-des-A,B-8-benzoyloxy-20-[4'-hydroxy-4'-methylpent-(1'E)-en-yl]-pregnane

: 1588410-78-9
(8S,20R)-des-A,B-8-benzoyloxy-20-[4'-(tertbutyldimethylsilyloxy)-4'-methyl-pent-(1'E)-en-yl]-pregnane

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -20 - 0 ℃; for 1h;
DOI:10.1016/j.steroids.2014.01.012

Reference yield:

: 1588410-77-8
(8S,20R)-des-A,B-8-benzoyloxy-20-[4'-hydroxy-4'-methylpent-(1'E)-en-yl]-pregnane

: 1588410-80-3
(20R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(tert-butyldimethyl-silyl)oxy]-19-nor-22(E)-ene-vitamin D3 tert-butyldimethylsilyl ether

Guidance literature:: Multi-step reaction with 4 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 1 h / -20 - 0 °C

2.1: sodium hydroxide / ethanol / 18 h / Reflux

3.1: dipyridinium dichromate; pyridinium p-toluenesulfonate / dichloromethane / 3 h / 20 °C

4.1: phenyllithium / tetrahydrofuran; dibutyl ether / 0.5 h / -20 °C / Inert atmosphere

4.2: 23 h / -78 - 4 °C / Inert atmosphere

With 2,6-dimethylpyridine; dipyridinium dichromate; pyridinium p-toluenesulfonate; phenyllithium; sodium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; dibutyl ether; 4.1: |Wittig-Horner Reaction;
DOI:10.1016/j.steroids.2014.01.012