Efficient activation of armed glycosyl trichloroacetimidates with Sm(OTf)(3) in the stereoselective glycosidation of saccharidic acceptors

Authors
Adinolfi, M Barone, G Guariniello, L Iadonisi, A
Citation
M. Adinolfi et al., Efficient activation of armed glycosyl trichloroacetimidates with Sm(OTf)(3) in the stereoselective glycosidation of saccharidic acceptors, TETRAHEDR L, 41(46), 2000, pp. 9005-9008
Citations number
16
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
46
Year of publication
2000
Pages
9005 - 9008
Database
ISI
SICI code
0040-4039(20001111)41:46<9005:EAOAGT>2.0.ZU;2-A
Abstract
Catalytic amounts of Sm(OTf)(3) activate armed glycosyl trichloroacetimidat es under very mild conditions. This reagent proved effective in promoting t he glucosylation of saccharidic accepters 2, 3, 4, and 5, possessing primar y or secondary hydroxyls, with the model donor 1. The stereoselectivity of these glycosidations can be controlled by a suitable choice of solvent. (C) 2000 Elsevier Science Ltd. All rights reserved.