First synthesis of diethyl N-acetyl-glycosamine-1- difluoromethylphosphonate from 2-nitroglycals as phosphate analog - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of Fluorine Chemistry Année : 2015

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

Résumé

Herein, we report the first access to diethyl glycosamine-1-difluoromethylphosphate as phosphate mimic. The diethyl 2-nitro-glycosides-beta-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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Dates et versions

hal-01149514 , version 1 (07-05-2015)

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Thierry Delaunay, Thomas Poisson, Philippe Jubault, Xavier Pannecoucke. First synthesis of diethyl N-acetyl-glycosamine-1- difluoromethylphosphonate from 2-nitroglycals as phosphate analog. Journal of Fluorine Chemistry, 2015, 171, pp.56-59. ⟨10.1016/j.jfluchem.2014.10.001⟩. ⟨hal-01149514⟩
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