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孕甾烷侧链的氰基硅烷化反应。20(R)-硅烷化氰醇的选择性合成及晶体结构

Cyanosilylation at pregnane side-chains. Selective synthesis and crystal structure of 20(R)-silylated cyanohydrins.

作者信息

Cruz Silva M Manuel, Andrade Lourdes C R, Paixão José A, de Almeida M José, e Melo M Luisa Sá

机构信息

Centro de Estudos Farmacêuticos, Lab. Química Farmacêutica, Faculdade de Farmácia, Universidade de Coimbra, Coimbra 3000, Portugal.

出版信息

Steroids. 2005 Mar;70(3):145-51. doi: 10.1016/j.steroids.2004.10.011.

DOI:10.1016/j.steroids.2004.10.011
PMID:15763592
Abstract

Trimethylsilylcyanide addition to different carbonyl moieties, i.e. saturated ketones, an enone and an aldehyde, at the steroid side-chain, was studied in the presence of a convenient catalyst. Depending on the nature of the carbonyl group, different outcomes were noticed. Saturated 20-keto pregnanes yielded epimerically pure silylated cyanohydrins, being the absolute configuration unambiguously established by X-ray crystallographic analysis.

摘要

在一种简便催化剂存在的情况下,研究了三甲基硅基氰化物添加到甾体侧链上不同的羰基部分,即饱和酮、烯酮和醛上的反应。根据羰基的性质,观察到了不同的结果。饱和的20-酮孕甾烷生成了差向异构体纯的硅烷基化氰醇,其绝对构型通过X射线晶体学分析明确确定。

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