SYNTHESIS OF A NEW BRANCHED-CHAIN HEXOPYRANOSYL NUCLEOSIDE - OXYMETHYL)-ALPHA-D-ERYTHRO-PENTOPYRANOSYL]-THYMINE

Authors
AUGUSTYNS K ROZENSKI J VANAERSCHOT A BUSSON R CLAES P HERDEWIJN P
Citation
K. Augustyns et al., SYNTHESIS OF A NEW BRANCHED-CHAIN HEXOPYRANOSYL NUCLEOSIDE - OXYMETHYL)-ALPHA-D-ERYTHRO-PENTOPYRANOSYL]-THYMINE, Tetrahedron, 50(4), 1994, pp. 1189-1198
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
4
Year of publication
1994
Pages
1189 - 1198
Database
ISI
SICI code
0040-4020(1994)50:4<1189:SOANBH>2.0.ZU;2-3
Abstract
A straightforward synthesis of the branched chain nucleoside 7 is desc ribed. This synthesis involves two stereoselective steps : introductio n of the hydroxymethyl group on the sugar is achieved by radical cycli zation of the (bromomethyl)dimethylsilyl ether of the allylic alcohol 8; the condensation reaction with thymine as base moiety resulted excl usively in the formation of the alpha anomer.