The first polymer-assisted solution-phase synthesis of deoxyglycosides

[GRAPHICS] 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.