Synthesis and Characterization of 5-Deoxy-3-O-methyl-5-C-[(R) - and (S)-phenylphosphinothioyl]-α- and β-D-xylopyranoses. The First Sugar Analogue Having a Phosphinothioyl Group in the Hemiacetal Ring

Treatment of 5-deoxy-5-iodo-1,2-O-isopropylidene-β-O-methyl-α-D-xylofuranose with ethyl phenylphosphinothioate in the presence of sodium hydride, followed by the reduction with sodium dihydrobis(2-methoxyethoxy)aluminate, and then with 0.5 M HCl–EtOH gave the title compounds, which were characterized as the 1,2,4-O-triacetates.