Synthesis of 5-thialdopentopyranoside via dithioacetal rearrangement and glycosidation to give pseudodisaccharides

Article abstract of DOI:10.1016/S0040-4039(00)73176-5

Rearrangement of acetylated 5-O-p-toluenesulfonyl-L-arabinose dibenzyl dithioacetal 10 gave benzyl 1,5-dithio-L-arabinopyranoside 6 which upon anomeric bromination followed by glycosidation led to pseudodisaccharide 20 containing a sulfur atom in the ring of the non-reducing unit. Similarly, benzyl 1,5-dithio-D-lyxopyranoside 17 was obtained from 5-O-p-toluenesulfonyl-D-lyxose dibenzyl dithioacetal 16.