Reaction of vinyl ethers with ArSCl adducts of D-glucal

Authors
Smoliakova, IP Han, MM Gong, JC Caple, R Smit, WA
Citation
Ip. Smoliakova et al., Reaction of vinyl ethers with ArSCl adducts of D-glucal, TETRAHEDRON, 55(15), 1999, pp. 4559-4572
Citations number
55
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
15
Year of publication
1999
Pages
4559 - 4572
Database
ISI
SICI code
0040-4020(19990409)55:15<4559:ROVEWA>2.0.ZU;2-Y
Abstract
Lewis acid mediated reactions of vinyl ethers with ArSCl adducts of benzyl protected D-glucal followed by quenching of the five-membered sulfonium sal t intermediates with external nucleophiles, H2O, MeOH, and n-Bu4NBH4, lead to a highly stereoselective formation of beta-C-glucopyranosides with diffe rent functional groups in the lateral chain. (C) 1999 Elsevier Science Ltd. All rights reserved.