This work presents the synthesis of glycosyl esters of 2-bromo-2-deoxy-D-he
xopyranose, having the alpha-D-manno (10 alpha-c alpha), beta-D-gluco (11a-
d beta) and alpha-D-gluco (11a,b alpha) configuration, by a stereoselective
reaction between phosphoroates 3-8 and carboxylic acids 9a-d. Derivatives
of 10a-c and 11a-d are formed in an overall quantitative yield, in an aprot
ic solvent in the presence of silver salts as a leaving group activator. Th
e phosphoroselenoate of 3 was obtained by the condensation reaction of the
triethylammonium salt of phosphoroseleno acid 2 with alpha-1,2-D-manno-pyra
nosyl dibromide 1 with high stereoselectivity. The structures of the compou
nds 3,10a-c and 11a-d were established by H-1 and C-13 NMR spectra and by e
lemental analyses. (C) 2000 John Wiley & Sons, Inc.