Stereospecific glycosylation of thiols by indium metal

ORGN 101

Bimal K. Banik, banik@panam.edu, Department of Chemistry, The University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78541 and Susanta Samajdar, The University of Texas M. D. Anderson Cancer Center, TX.

Glycosylation of thiols is an attractive area of research because of the biological activities of S-glycosides.  Our ongoing studies of metal-mediated chemical transformations have demonstrated various indium-induced reactions.  During the course of study, we have discovered indium metal-mediated stereospecific synthesis of b-glycosides using bromosugar and thiolsThis can be explained by a SN2-type reaction of thiol with bromosugar.  However, the role of indium in promoting the formation of b-glycosides with 2-acetoxy and 2-deoxy bromosugar is not properly understood.