Facile preparation of glycomimetics from uronic acids

Abstract

The following work describes facile methods for the preparation of amino sugar analogs of N-acetyl-2-amino-2-deoxy-D-mannopyranose uronic acid (D-ManAcA). Two main approaches were investigated in the synthesis of N-glycosides. Staudinger and aza-Wittig approaches were used to synthesize glucosyl amides and imines. Another approach to the synthesis of N-glycosides involved the application of 1,3-dipolarcycloadditions of azides and alkynes in the presence of a Cu(I) catalyst. The synthesis of O-glycosides and C-glycosides of the methyl ester of glucuronic acid were studied in regard to the development of high yielding, stereospecific mimetic syntheses.