An Efficient Stereospecific Synthesis of 1-α-C-glycosylphosphonic Acid

Abstract

The convenient stereospecific synthesis of the isosteric phosphono analogue of N-acetylglucosamine was described.Especially the α analogue of N-acetyl-D-glucosamine 1-phosphoric acid 1 has been synthesized starting from N-acetyl-D-glucosamine through the following reaction: Stereoselective radical α-1-C-allylation of 1-chloro-N-acetyl-D-glucosamine,catalytic double bond isomerization, Lemieux-Johnson oxidation, addition reaction of dialkylphosphonates, radicaldehydroxylation, and removal of protecting group. Final compound was fully characterized by NMR (1H, 13C, 19F and 31P) andHRMS experiments.