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.
(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.
Ciuffreda
Pierangela
P
Dipartimento di Scienze Precliniche LITA Vialba, Via G.B. Grassi, 74-20157 Milano, Italy.
Casati
Silvana
S
Bollini
Deborah
D
Santaniello
Enzo
E
D003903:Deuterium; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D011278:Pregnanes / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013261:Sterols / Q000138:chemical synthesis* / Q000737:chemistry*
C478779:3-(tert-butyldimethylsilanyloxy)-20-methylpregn-5-en-21-ol; D017646:Organosilicon Compounds; D011278:Pregnanes; D013261:Sterols; D003903:Deuterium