Synthesis and structural analysis of 6-deoxy-6-hydroxyphosphinyl- d-fructopyranose derivatives

[Display omitted] 3,4-Di- O-benzyl-6-deoxy-6-diethoxyphosphinyl-1,2- O-isopropylidene-β- d-fructofuranose ( 13) was prepared from the known 1,2- O-isopropylidene-6- O-tosyl-β- d-fructofuranose in five steps. Reduction of 13 with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by the action of hydrochloric acid and then hydrogen peroxide, afforded the 6-deoxy-6-hydroxyphosphinyl- d-fructopyranose derivative. This was converted into the 1,2,3,4,5-penta- O-acetyl-6-deoxy-6-methoxyphosphinyl- d-fructopyranoses, whose structure and conformation were established by 1H NMR spectroscopy.