Synthesis of (difluoromethyl)phosphonate azasugars designed as inhibitors for glycosyl transferases

Abstract

Polyhydroxylated pyrrolidines (azasugars) bearing a (difluoromethylene)phosphonate group at the pseudoanomeric position are prepared by nucleophilic opening of arabino-, ribo- and xylo-furanosylamine with diethyl (lithiodifluoromethyl)phosphonate followed by cyclisation of the amino phosphonate products obtained.

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