Chemical interconversions of 4-cyanophenyl 1,5-dithio-β-d-xylopyranoside (Beciparcil®): structural modification at the C-4 position

The title dithioxyloside 1, an orally active antithrombotic agent, as its 2,3-isopropylidene acetal, was converted into the corresponding glycos-4-ulose, which served as precursor via reduction to the 4-epimer of 1 and via oximation–reduction to the 4-acetamido-4-deoxy 4-epimer of 1.