Oxidations Based on Dimethyl Sulfoxide

On treatment with dimethyl sulfoxide-acetic anhydride followed by sequential oximation, reduction, detritylation, and acid hydrolysis, a tetra-(6-0-trityl)-cyclohexaamylose was reported to afford 2-amino-2-deoxy-D-glucose, in addition to D-glucose, indicating459 that 

Useful syntheses of D- and L-lyxose from 1,3-O-benzylidene-D- and L-arabinitol have been achieved through the highly selective oxidation of the primary hydroxyl groups by dimethyl sulfoxide-dicyclohexylcarbodiimide.463 Oxidation of but one of the two (equivalent) hydroxyl groups in 1,3,4,6-tetra-O-benzyl-D-mannitol464 and l,6-di-0-benzyl-2,5-0-methylene-D-mannitol465 was possible with dimethyl sulfoxide-acetic anhydride. 

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