EFFICIENT TRANSFORMATION OF THYMIDINE INTO 2',3'-DIDEHYDRO-2',3'-DIDEOXY-THYMIDINE (D4T) INVOLVING OPENING OF A 2,3'-ANHYDRO DERIVATIVE BY PHENYLSELENOL

Authors
BECOUARN S CZERNECKI S VALERY JM
Citation
S. Becouarn et al., EFFICIENT TRANSFORMATION OF THYMIDINE INTO 2',3'-DIDEHYDRO-2',3'-DIDEOXY-THYMIDINE (D4T) INVOLVING OPENING OF A 2,3'-ANHYDRO DERIVATIVE BY PHENYLSELENOL, Nucleosides & nucleotides, 14(6), 1995, pp. 1227-1232
Citations number
19
Categorie Soggetti
Biology
Journal title
Nucleosides & nucleotides → ACNP
ISSN journal
07328311
Volume
14
Issue
6
Year of publication
1995
Pages
1227 - 1232
Database
ISI
SICI code
0732-8311(1995)14:6<1227:ETOTI2>2.0.ZU;2-S
Abstract
A new, high-yielding method for introduction of the selenophenyl resid ue at the 3'- position of thymidine is reported. This reaction avoided any strongly basic or reductive reagent, thus allowing the use of ben zoate ester as a protective group at O-5'. Further oxidation-eliminati on sequence followed by basic deprotection afforded 2',3'-didehydro-2' ,3'-dideoxythymidine (D4T) in 67.5 % overall yield from thymidine.