Stereospecific Synthesis of the Phosphono Analogues of α- and β-D-Glucose 1-Phosphate

Article abstract of DOI:10.1021/jo00144a011

The present paper describes the convenient stereospecific synthesis of the analogues of α- and β-D-glucose 1-phosphate.The β analogue, (1-deoxy-β-D-glucopyranosyl)methanephosphonic acid, was synthesized by treatment of 2,6-anhydro-1-bromo-1-deoxy-3,4,5,7-tetra-O-acetyl-D-glycero-D-gluco-heptitol with triethyl phosphite, followed by deethylation of the obtained diethyl (1-deoxy-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)methanephosphonate and deacetylation with ion-exchange resin.The α analogue, (1-deoxy-α-D-glucopyranosyl)methanephosphonic acid, was synthesized by starting from 2,3,4,6-tetra-O-benzyl-D-glucose through the followin g sequence: Wittig reaction with methylenetriphenylphosphorane, mercuriocyclization, bromodemercuriation, Arbuzov reaction, and removal of the protecting groups.