An efficient synthesis of D-mannoheptulose via oxidation of an olefinated sugar with potassium permanganate in aqueous acetone

An efficient three-step synthesis of D-mannoheptulose was successfully accomplished from 2,3,4,5,6-penta-O-benzyl-D-mannose. First, an olefinated sugar was prepared from 2,3,4,5,6-penta-O-benzyl-D-mannose via a Wittig reaction. Second, the key step, a 2-hydroxyoxirane product was unexpectedly obtained by oxidation of the olefinated sugar with potassium permanganate in aqueous acetone. Finally D-mannoheptulose was synthesized through debenzylation and hydrolysis in an overall yield of 39%. (C) 2009 Published by Elsevier Ltd.