SYNTHESIS OF PSEUDONUCLEOSIDES CONTAINING CHIRAL SULFAHYDANTOINS AS AGLYCONE(II)

Authors
DEWYNTER G AOUF N REGAINIA Z MONTERO JL
Citation
G. Dewynter et al., SYNTHESIS OF PSEUDONUCLEOSIDES CONTAINING CHIRAL SULFAHYDANTOINS AS AGLYCONE(II), Tetrahedron, 52(3), 1996, pp. 993-1004
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
3
Year of publication
1996
Pages
993 - 1004
Database
ISI
SICI code
0040-4020(1996)52:3<993:SOPCCS>2.0.ZU;2-5
Abstract
A series of chiral sulfahydantoins have been synthesized by alkaline c yclization starting from N-sulfamylaminoacid methyl esters. Regioselec tive glycosylation of these pseudopyrimidic heterocycles was carried o ut with a benzyl protecting group on the N-sulfonylcarbamic position. Best glycosylation results were obtained by preliminary silylation of sulfahydantoins, and their condensation with a tetracylribofuranose wh ich yielded the pseudonucleosides in a beta-anomeric configuration.