(24R)-24-乙基-5α-胆甾烷-3β-醇和(24S)-24-乙基-胆甾-5,22-二烯-3β-醇的4α-甲基和4β-甲基异构体的化学合成、光谱性质及色谱分析

Chemical synthesis, spectral properties, and chromatography of 4alpha-methyl and 4beta-methyl isomers of (24R)-24-ethyl-5alpha-cholestan-3beta-ol and (24S)-24-ethyl-cholesta-5,22-dien-3beta-ol.

作者信息

Knapp F F, Schroepfer G J

出版信息

Steroids. 1975 Sep;26(3):339-57. doi: 10.1016/0039-128x(75)90079-3.

PMID:1198622

Abstract

Described herein are chemical syntheses of the following compounds: 4-methyl-(24S)-24-ethyl-cholesta-4,22-dien-3-one, 4,4-dimethyl-(24S)-24-ethyl-cholesta-5,22-dien-3-one, 4beta-methyl-(24R)-24-ethyl-5alpha-cholestan-3beta-ol, 4alpha-methyl-(24R)-24-ethyl-5alpha-cholestan-3beta-ol, 4alpha-methyl-(24S)-24-ethyl-5alpha-cholest-22-en-3beta-ol, 4-methyl-6beta-bromo-(24S)-24-ethyl-cholesta-4,22-dien-3-one, 4alpha-methyl-(24S)-24-ethyl-cholesta-5,22-dien-3beta-ol, 4alpha,5alpha-epoxy-(24S)-24-ethyl-cholesta-4,22-dien-3beta-yl acetate, 4beta-methyl-(24S)-24-ethyl-cholest-22-en-3beta,5alpha-diol, 4beta-methyl-5alpha-hydroxy-(24S)-24-ethyl-cholest-22-en-3beta-yl acetate, 4beta-methyl-(24S)-24-ethyl-cholesta-5,22-dien-3beta-yl acetate and 4beta-methyl-(24S)-24-ethyl-cholesta-5,22-dien-3beta-ol. Chromatographic, nuclear magnetic resonance, and mass spectral data are presented for the compounds under consideration.

摘要

本文描述了以下化合物的化学合成方法

4-甲基-（24S）-24-乙基-胆甾-4,22-二烯-3-酮、4,4-二甲基-（24S）-24-乙基-胆甾-5,22-二烯-3-酮、4β-甲基-（24R）-24-乙基-5α-胆甾烷-3β-醇、4α-甲基-（24R）-24-乙基-5α-胆甾烷-3β-醇、4α-甲基-（24S）-24-乙基-5α-胆甾-22-烯-3β-醇、4-甲基-6β-溴-（24S）-24-乙基-胆甾-4,22-二烯-3-酮、4α-甲基-（24S）-24-乙基-胆甾-5,22-二烯-3β-醇、4α,5α-环氧-（24S）-24-乙基-胆甾-4,22-二烯-3β-基乙酸酯、4β-甲基-（24S）-24-乙基-胆甾-22-烯-3β,5α-二醇、4β-甲基-5α-羟基-（24S）-24-乙基-胆甾-22-烯-3β-基乙酸酯、4β-甲基-（24S）-24-乙基-胆甾-5,22-二烯-3β-基乙酸酯和4β-甲基-（24S）-24-乙基-胆甾-5,22-二烯-3β-醇。文中给出了所讨论化合物的色谱、核磁共振和质谱数据。