The synthesis of cyclic imidates from amides of glucuronic acid and investigation of glycosidation reactions

Linda Cronin; Manuela Tosin; Helge Müller-Bunz; Paul V Murphy

doi:10.1016/j.carres.2006.10.023

The synthesis of cyclic imidates from amides of glucuronic acid and investigation of glycosidation reactions

Carbohydr Res. 2007 Jan 15;342(1):111-8. doi: 10.1016/j.carres.2006.10.023. Epub 2006 Nov 1.

Authors

Linda Cronin¹, Manuela Tosin, Helge Müller-Bunz, Paul V Murphy

Affiliation

¹ UCD School of Chemistry and Chemical Biology, Centre for Synthesis and Chemical Biology, Conway Institute of Biomolecular and Biomedical Research, University College Dublin, Belfield, Dublin 4, Ireland.

PMID: 17123491
DOI: 10.1016/j.carres.2006.10.023

Abstract

The synthesis of novel cyclic glycosyl imidates and an investigation of their potential as donors in glycosidation reactions is described. The results show that 1,2-cis glycosides obtained from the reactions of glycosyl acetates or cyclic imidates, each derived from amides of glucuronic acid, result from the anomerisation of initially formed 1,2-trans glycosides.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amides / chemistry*
Glucuronic Acid / chemistry*
Glycosides / chemistry*
Glycosylation
Imidoesters / chemical synthesis*
Imidoesters / chemistry

Substances

Amides
Glycosides
Imidoesters
Glucuronic Acid