Synthesis of 2',3'-dideoxy-3',3'-difluoro and 2',3'-dideoxy-2',2'- difluoro-pyranosyl nucleosides analogues of gemcitabine

Article abstract of DOI:10.1016/S0040-4020(99)00468-8

The gem-difluoronucleosides 1 and 2, pyranosyl analogues of gemcitabine, have been synthesized from D-mannose and D-glucose respectively. The key steps were the formation of the difluoromethylene group by reaction of the corresponding ulose with DAST, and the glycosylation.