Approaches to the synthesis of CF2-analogues of 2-deoxy-2-aminoglycosides

The preparation of a fluorinated C-glycosidic analogue of a 2-deoxy-2-acetamido-d-altrose is described. The synthetic sequence involves the addition of a difluoroenoxysilane to a d-glucal, an epoxidation of the resulting unsaturated CF2-glycoside and a ring-opening reaction with TMSN3. An Overman rearrangement of the unsaturated intermediate is also described.