Anomeric activation of thioglycosides and preparation of deoxyglycosides using polymer-bound iodate(I) complexes

New thiophilic polymer-bound haloate(l) complexes are presented which are well suited for the polymer-assisted solution-phase activation of 2-deoxythioglycosides. In the presence of alcohols 2-deoxyglycosides are obtained in yields between 60 and 95%. Isolation of the target glycosides is further simplified by removing the byproduct diphenyldisulfide by reductive work-up. Here also a polymer-bound reagent, namely borohydride exchange resin, served as a tool for sequestering the sulfur-containing impurities. (C) 2003 Elsevier Science Ltd. All rights reserved.