Glycosylation Based on Glycosyl Phosphates as Glycosyl Donors

Hariprasad Vankayalapati; Shende Jiang; Gurdial Singh

doi:10.1055/s-2002-19315

ACCOUNT

Glycosylation Based on Glycosyl Phosphates as Glycosyl Donors

Hariprasad Vankayalapati, Shende Jiang, Gurdial Singh*
Department of Chemistry, University of Sunderland, Sunderland SR1 3SD, UK
Fax: +44(191)5153148; e-Mail: gurdial.singh@sunderland.ac.uk;

Abstract

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Abstract

Glycosyl phosphates have emerged as useful glycosyl donors for stereoselective glycosidic bond formation in the synthesis of oligosaccharides. In this account, we describe some of our work in developing and further expanding this methodology, particularly with the use of propane-1,3-diyl phosphate as the anomeric leaving group. We have studied the reactions of several glycosyl propane-1,3-diyl phosphates with or without C-2 participating groups with a range of glycosyl acceptors in the presence of trimethylsilyl triflate in either stoichiometric or catalytic amount, and demonstrated their application in the synthesis of several disaccharides and also the synthesis of some trisaccharides.

Key words

carbohydrates - glycosides - glycosyl phosphates - glycosylation - oligosaccharides

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References

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