1,6-anhydro-1(6)-thio-L-iditol and -D-mannitol, and some derivatives thereof

Starting from 1,2:5,6-dianhydro-3,4-O-isopropylidene-L-iditol (1) and -D-mannitol (6), respectively, the corresponding 1,6-anhydro-1,(6)-thio derivatives (2a and 7a) were synthesized. The discrepancy in the yields obtained, as well as the different behavior of their methylated derivatives (2e and 7c) towards acid hydrolysis, could be explained by steric factors. The di-O-mesyl derivatives 3d and 12c were unstable compounds, and showed no ulcerostatic activity, unlike the D-glucitol analog.