Selective Reduction Leading to 3,5-cis-3-Aminosugars: Synthesis and Stereoselective Glycosylation.

ABSTRACT

Synthesis of 3,5-cis-3-amino glycals with a cis-fused cyclic sulfamidate group has been achieved by selective reduction of sulfamidate ketimine groups. The efficient access to the structurally unique glycals allowed the subsequent divergent synthesis of various naturally occurring 3-amino-2,3,6-trideoxysugars. In addition, Lewis acid-promoted glycosylation of the glycals provided a simple solution for the stereoselective installation of O- and C-linked aglycons on the amino sugar scaffolds.