An efficient synthesis of mixed beta-carbonates of acyl-protected sugar and their decarboxylative glycosidation promoted by trimethylsilyl trifluoromethanesulfonate

Authors
Azumaya, I Niwa, T Kotani, M Iimori, T Ikegami, S
Citation
I. Azumaya et al., An efficient synthesis of mixed beta-carbonates of acyl-protected sugar and their decarboxylative glycosidation promoted by trimethylsilyl trifluoromethanesulfonate, TETRAHEDR L, 40(25), 1999, pp. 4683-4686
Citations number
25
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
25
Year of publication
1999
Pages
4683 - 4686
Database
ISI
SICI code
0040-4039(19990618)40:25<4683:AESOMB>2.0.ZU;2-B
Abstract
Mixed beta-carbonates of acyl-protected sugar are stereoselectively prepare d by using an N-succinimidyl group for activation of the acceptor alcohol c arbonate. The glycosyl carbonates are smoothly decarboxylated by trimethyls ilyl trifluoromethanesulfonate (Me3SiOTf) to give beta-glycosides preferent ially in high yields. (C) 1999 Elsevier Science Ltd. All rights reserved.