Towards the Synthesis of Aureolic Acid Analogue Conjugates: Synthesis and Glycosidation Reactions of 3-O-Acetyl-4-azido-2,4,6-trideoxy-L-glucopyranose Derivatives

A stereoselective synthesis of 3-O-acetyl-4-azido-glucopyranose (6) is described. The derived anomeric acetate (13), and especially the thioglycoside (14), are demonstrated to be good donors for synthesis of α-glycosides of (6). Donor (14) was used in the synthesis of trisaccharide (21), which is targeted for use in the synthesis of the aureolic acid trisaccharide conjugate analogue (5).