Tin-mediated regioselective acylation of unprotected sugars on solid phase

Authors
Peri, F Cipolla, L Nicotra, F
Citation
F. Peri et al., Tin-mediated regioselective acylation of unprotected sugars on solid phase, TETRAHEDR L, 41(44), 2000, pp. 8587-8590
Citations number
12
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
44
Year of publication
2000
Pages
8587 - 8590
Database
ISI
SICI code
0040-4039(20001028)41:44<8587:TRAOUS>2.0.ZU;2-C
Abstract
Methyl alpha -D-glucopyranoside, methyl alpha -D-mannopyranoside and methyl beta -D-galactopyranoside bound on O-6 to a copolystyrene-DVB resin throug h a trityl ether linker, have been regioselectively acylated with benzoyl c hloride after treatment with Bu2SnO and stannylene formation on solid phase . The benzoylation reactions proved to be highly regioselective affording 2 -O benzoyl derivatives for glucose and 3-O benzoyl derivatives for galactos e and mannose with high yield. (C) 2000 Published by Elsevier Science Ltd.