A NEW SYNTHESIS OF METHYL β-D-GULOPYRANOSIDE

Abstract

The oxidation of 1 mole of β-D-glycero-D-gulo-heptopyranoside with 1 mole of sodium metaperiodate, followed by reduction with sodium borohydride, gave rise to crystalline methyl β-D-gulopyranoside. The method provides a new synthetic route to the D-guloside and, thence, to D-gulose. The possibility of utilizing this reaction scheme as a general convenient method for preparing the relatively rare aldohexoses as well as for "labelling" carbon atom 1 of these compounds is discussed.