Synthesis of 1,2,3,4-tetra- O-acetyl-5-deoxy-5- C-[( R)- and ( S)-phenylphosphinyl]-α- and -β- d-xylopyranoses

Abstract

Abstract Treatment of methyl 5-deoxy-5- C -(diethoxyphosphinyl)-2,3- O -isopropylidene-β- d -ribofuranoside with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by hydrogen peroxide, mineral acid, and hydrogen peroxide, gave 5-deoxy-5- C -(hydroxyphosphinyl)-α,β- d -ribopyranoses in 40–45% overall yield. The structures of these sugar analogs were effectively established on the basis of the mass and 400-MHz, 1 H-n.m.r. spectra of the title compounds, derived by treatment with diazomethane and then acetic anhydride in pyridine.