Synthesis of (20S)-[7,7,21,21-2H4]-3beta-(tert-butyldimethylsilanyloxy)-20-methyl-pregn-5-en-21-ol, a useful intermediate for the preparation of deuterated isotopomers of sterols.

Abstract:

:(20S)-[7,7,21,21-2H(4)]-3beta-(tert-Butyldimethylsilanyloxy)-20-methyl-pregn-5-en-21-ol, an intermediate for the preparation of deuterated isotopomers of sterols to be used as standards for biomedical studies, was prepared by reduction with dichloroaluminum deuteride of ethyl (20S)-3beta-(tert-butyldimethylsilanyloxy)-7-oxo-pregn-5-en-20-carboxylate. Using controlled experimental conditions, it has also been shown that the dichloroaluminum hydride reduction of a 7-keto steroid affords the corresponding 7beta-hydroxy derivative in a highly stereoselective manner.

journal_name

Steroids

journal_title

Steroids

authors

Ciuffreda P,Casati S,Bollini D,Santaniello E

doi

10.1016/s0039-128x(02)00172-1

subject

Has Abstract

pub_date

2003-02-01 00:00:00

pages

193-8

issue

2

eissn

0039-128X

issn

1878-5867

pii

S0039128X02001721

journal_volume

68

pub_type

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