CONVENIENT SYNTHESIS OF ALPHA-2-DEOXYGLYCOSIDE AND BETA-2-DEOXYGLYCOSIDE

Authors
CASTROPALOMINO JC SCHMIDT RR
Citation
Jc. Castropalomino et Rr. Schmidt, CONVENIENT SYNTHESIS OF ALPHA-2-DEOXYGLYCOSIDE AND BETA-2-DEOXYGLYCOSIDE, Synlett, (5), 1998, pp. 501
Citations number
36
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
5
Year of publication
1998
Database
ISI
SICI code
0936-5214(1998):5<501:CSOAAB>2.0.ZU;2-O
Abstract
Readily available O-thiobenzoyl-manno-pyranosyl)trichloroacetimidate 4 a gave with glucosides 7 and 8 as glycosyl accepters exclusively alpha -linked disaccharides 9 alpha and 10 alpha. Accordingly, from O-(2-O-t hiobenzoyl-glucopyranosyl)trichloroacet imidate 4b exclusively beta-li nked disaccharides 9 beta and 10 beta were obtained. Radical initiated deoxygenation with Bu3SnH/AIBN directly furnished 2-deoxyglycosides 1 1 alpha,beta and 12 alpha,beta.