Efficient syntheses of beta-cyanosugars using glycosyl iodides derived from per-O-silylated mono- and disaccharides

Authors
Bhat, AS Gervay-Hague, J
Citation
As. Bhat et J. Gervay-hague, Efficient syntheses of beta-cyanosugars using glycosyl iodides derived from per-O-silylated mono- and disaccharides, ORG LETT, 3(13), 2001, pp. 2081-2084
Citations number
16
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
13
Year of publication
2001
Pages
2081 - 2084
Database
ISI
SICI code
1523-7060(20010628)3:13<2081:ESOBUG>2.0.ZU;2-R
Abstract
[GRAPHICS] Reported herein is a general method for the efficient syntheses of a variet y of beta -cyano glycosides through the activation of per-O-trimethylsllyl glycosides with TMSI to form alpha -glycosyl iodides, which undergo S(N)2-t ype displacement when treated with tetrabutylammonium cyanide. The cyanogly cosides were reduced under mild conditions using NaBH4 in the presence of c atalytic CoCl2(H2O)(6) in THF/H2O to give the corresponding aminomethyl gly cosides.