Stereoselective synthesis of 2-deoxy-beta-galactosides via 2-deoxy-2-bromo- and 2-deoxy-2-iodo-galactopyranosyl donors

Timothy B Durham; William R Roush

doi:10.1021/ol034393t

Stereoselective synthesis of 2-deoxy-beta-galactosides via 2-deoxy-2-bromo- and 2-deoxy-2-iodo-galactopyranosyl donors

Org Lett. 2003 May 29;5(11):1871-4. doi: 10.1021/ol034393t.

Authors

Timothy B Durham¹, William R Roush

Affiliation

¹ Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.

PMID: 12762674
DOI: 10.1021/ol034393t

Abstract

[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.

Publication types

Research Support, U.S. Gov't, P.H.S.

MeSH terms

Carbohydrate Conformation
Carbohydrate Sequence
Galactosides / chemical synthesis*
Glycosylation
Indicators and Reagents
Oligosaccharides / chemical synthesis
Oligosaccharides / chemistry
Stereoisomerism

Substances

Galactosides
Indicators and Reagents
Oligosaccharides