Abstract
In this work, synthesis and characterization of a series of D-Mannitol derivatives with sulfite 2a-d and sulfate 3a-d moieties have been investigated. The method entails a two-step synthesis. The first step involves the Sharpless-type reaction of DIOL 1a-d with SOCl2 in CH2Cl2 in the presence of Et3N to afford the intermediate sulfite derivatives 2a-d in good yield. The second step includes the oxidation reaction of the resulting intermediate in the presence of NaIO4 in a mixture of CCl4/CH3CN/H2O (3/3/2 ratio) in the presence of catalytic amount of RuCl3 center dot H2O to afford the desired sulfate moiety 3a-d in a moderate to high yield (66-96%). The structures of all newly synthesized compounds have been elucidated by H-1, C-13 NMR, GCMS, and IR spectrometry. (C) 2013 Production and hosting by Elsevier B.V. on behalf of King Saud University.