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Paper | Special issue | Vol 84, No. 2, 2012, pp.1067-1079
Published online, 2nd September, 2011
DOI: 10.3987/COM-11-S(P)84
Synthesis of Novel Oligosaccharides Based on 1,4-Dioxanyloxy 3-Oxasugars

Margaret Morozova, Sonali Wickremasinghe, and Mark A. Rizzacasa*

*School of Chemistry, The Bio21 Institute, The University of Melbourne, Building 102, 30 Flemington Road
Melbourne, Victoria 3010, Australia

Abstract

The synthesis of a new family of di and tri-3-oxaoligosaccharides based on the 1,4-dioxanyloxy or 3-oxapseudosugar moiety is described. The approach involved the glycosylation of trichloroacetamidate donors with acceptor alcohols to provide 3-oxadi- and trisaccharides. In all cases, the glycosylation was highly stereoselective providing the 1α anomers exclusively.