Efficient palladium(0)-catalyzed synthesis of alkenyl 1-thioglycosides andthiodisaccharides

Authors
Zawisza, A Kryczka, B Lhoste, P Porwanski, S Sinou, D
Citation
A. Zawisza et al., Efficient palladium(0)-catalyzed synthesis of alkenyl 1-thioglycosides andthiodisaccharides, J CARB CHEM, 19(7), 2000, pp. 795-804
Citations number
24
Categorie Soggetti
Chemistry & Analysis
Journal title
JOURNAL OF CARBOHYDRATE CHEMISTRY
ISSN journal
07328303 → ACNP
Volume
19
Issue
7
Year of publication
2000
Pages
795 - 804
Database
ISI
SICI code
0732-8303(2000)19:7<795:EPSOA1>2.0.ZU;2-2
Abstract
Unsaturated thiodisaccharides are obtained in good yields by alkylation of ethyl alpha-Q-Delta(2)-glycosides, having a leaving group at C-4, with vari ous thiocarbohydrates in the presence of a catalytic amount of palladium(0) . The reaction is regio- and stereospecific for the alpha-erythro enoside, and only stereospecific in the case of the alpha-threo enoside, alkylation occurring at C-4 and C-2. In all cases, only the beta-anomer is formed.