Stannylene acetal-mediated regioselective open glycosylation of methyl beta-D-galactopyranoside and methyl alpha-L-rhamnopyranoside

Authors
Kaji, E Harita, N
Citation
E. Kaji et N. Harita, Stannylene acetal-mediated regioselective open glycosylation of methyl beta-D-galactopyranoside and methyl alpha-L-rhamnopyranoside, TETRAHEDR L, 41(1), 2000, pp. 53-56
Citations number
17
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
1
Year of publication
2000
Pages
53 - 56
Database
ISI
SICI code
0040-4039(20000101)41:1<53:SAROGO>2.0.ZU;2-W
Abstract
Open glycosylation of stannylated methyl beta-D-galactopyranoside with per- O-benzoyl or -pivaloylglucopyranosyl bromide and -glucuronyl bromide, promo ted by Ag-silica alumina, afforded regio- and stereoselectively glycosyl-be ta(1-->6)-galactose and its orthoester derivative in good yield. Similar gl ycosylation of unprotected methyl alpha-L-rhamnopyranoside with per-O-pival oylglucuronyl bromide provided glucuronyl-beta(1-->3)-rhamnose in moderate yield. (C) 1999 Elsevier Science Ltd. All rights reserved.