(20S)-[7,7,21,21-H-2(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.

Synthesis of (20S)-[7,7,21,21-H-2(4)]-3 beta-(tert-butyldimethylsilanyloxy)-20-methyl-pregn-5-en-21-ol, a useful intermediate for the preparation of deuterated isotopomers of sterols / P. Ciuffreda, S. Casati, D. Bollini, E. Santaniello. - In: STEROIDS. - ISSN 0039-128X. - 68:2(2003), pp. 193-198.

Synthesis of (20S)-[7,7,21,21-H-2(4)]-3 beta-(tert-butyldimethylsilanyloxy)-20-methyl-pregn-5-en-21-ol, a useful intermediate for the preparation of deuterated isotopomers of sterols

P. Ciuffreda
Primo
;
S. Casati
Secondo
;
E. Santaniello
Ultimo
2003

Abstract

(20S)-[7,7,21,21-H-2(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.
(20S)-[7,7,21,21- 2H4 ]-3β-(tert-Butyldimethylsilanyloxy)-20-methyl-pregn-5-en-21-ol; 7β-Hydroxysterols; Deuterated isotopomers; Deuterated sterols; Dichloroaluminum deuteride
Settore BIO/10 - Biochimica
2003
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/5240
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