First synthesis of the phosphono analogue of N-acetyl-α-D-mannosamine 1-phosphate

Abstract

Recation of 2,3,5-tri-O-benzyl-D-arabinose with divinylzinc, and subsequent mercuriocyclisation and iododemercuriation stereoselectivity affords the α-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 hydrogenation and acetylation, afford the phosphono analogue of N-acetyl-α-D-mannosamine 1-phosphate.