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

Abdullah M.A. Al Majid, Assem Barakat, Yahia Nasser Mabkhot, Mohamed H.M. Al-Agamy
2016 Journal of Saudi Chemical Society  
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 SOCl 2 in CH 2 Cl 2 in the presence of Et 3 N 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 NaIO 4 in a mixture of CCl
more » ... /CH 3 CN/H 2 O (3/3/2 ratio) in the presence of catalytic amount of RuCl 3 AEH 2 O 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 1 H, 13 C NMR, GCMS, and IR spectrometry. ª 2013 Production and hosting by Elsevier B.V. on behalf of King Saud University.
doi:10.1016/j.jscs.2013.10.011 fatcat:ttbwupd7dzbafa4fhviboiik5y