Synthesis, and characterization of a new series of sulfite and sulfate derivatives of d-Mannitol

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·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 1H, 13C NMR, GCMS, and IR spectrometry.

Keywords

• d-Mannitol
• Sulfite
• Sulfate
• Sulfation
• Sharpless oxidation