Glycal-mediated syntheses of enantiomerically pure 3-azido-2,3-dideoxy-hexopyranosides and 3-amino-2,3-dideoxy-hexopyranolactones

Abstract Methodology for the conversion of two commercially available glycals, d -galactal and d -glucal, into 3-azido-2,3-dideoxy-hexopyranosides and 3-amino-2,3-dideoxy-hexopyranolactones is reported. Using this strategy, templates suitable in combinatorial chemistry for the construction of a number of interesting biologically active molecules have been prepared. Key features of this strategy include the development of an efficient and original reaction sequence for the differential protection of the oxygen functionalities, the regio- and stereoselective introduction of the azido group, and the chemoselective oxidation of the acetal group.