FIRST SYNTHESIS OF THE PHOSPHONO ANALOG OF N-ACETYL-ALPHA-D-MANNOSAMINE 1-PHOSPHATE

Reaction of 2,3,5-tri-O-benzyl-D-arabinose with divinylzinc, and subse quent mercuriocyclisation and iododemercuriation stereoselectivity aff ords the alpha-C-glucopyranosyl iodide 3 with a free hydroxy group at C-2; temporary protection of the free hydroxy group, treatment of the iodide with triethylphosphite to afford the corresponding phosphonate, deprotection of the hydroxy group, oxidation, oximation, catalytic hy drogenation and acetylation, afford the phosphono analogue of N-acetyl -alpha-D-mannosamine 1-phosphate.