Stereoselective synthesis of 2-deoxy-beta-galactosides via 2-deoxy-2-bromo- and 2-deoxy-2-iodo-galactopyranosyl donors.
[reaction: see text] A series of 2-bromo- and 2-iodo-galactopyranosyl acetates and trichloroacetimidates were evaluated as glycosyl donors for the synthesis of 2-deoxygalactopyranosides. The best selectivity for the beta-glycosidic linkage was achieved by using 6-deoxy-3,4-carbonate-protected galactosyl donors.
Durham
Timothy B
TB
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.
Roush
William R
WR
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D005697:Galactosides / Q000138:chemical synthesis*; D006031:Glycosylation; D007202:Indicators and Reagents; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D005697:Galactosides; D007202:Indicators and Reagents; D009844:Oligosaccharides