First synthesis of diethyl N-acetyl-glycosamine-1-difluoromethylphosphonate from 2-nitroglycals as phosphate analog

Herein, we report the first access to diethyl glycosamine-1-difluoromethylphosphate as phosphate mimic. The diethyl 2-nitro-glycosides-β-1-difluoromethylphosphonate were obtained from a Michael addition of diethyl(difluoro-(trimethylsilyl)methyl)phosphonate on 2-nitroglycals in the presence of a fluoride promoter in good to excellent yields. A subsequent reduction of the nitro group leads to the N-acetyl glycosides derivative giving a straightforward access to phosphate analogs.