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A glycosylation protocol for the synthesis of 2-deoxyglycosides has been de
veloped which is based on the use of polymer-bound reagents. Glycals are tr
ansformed into 2-iodoglycosyl acetates using polymer-bound bis(acetoxy)ioda
te(1) complex (1). Activation of the anomeric center is achieved by employi
ng polymer-bound silyl triflate (2). In the presence of different glycosyl
acceptors, 2-deoxy-2-iodoglycosides are generated in very good yields. Furt
hermore, it is shown that this method can be embedded in multistep sequence
s toward glycosylated testosterone and rhodinosyl-olivosyl-olivoside.