Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1313601 | Journal of Fluorine Chemistry | 2015 | 4 Pages |
•Diastereoselective Michael addition of TMSCF2P(O)(OEt)2 onto 2-nitroglycals.•Replacement of an oxygen by the difluoromethylene group to mimic the anomeric linkage.•First access to N-acetyl-glycosamine-1-difluorophosphonate, as potent glycomimetics.
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.
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