(Chemical Equation Presented) Reaction of a galactosylated 2-C-(hydroxymethyl)-tetrofuranose with paramolybdate ion-exchange resin in aqueous solution at 67°C gave an equilibrium mixture containing the reactant aldofuranose (42%) and a 2-ketopentofuranose galactosylated at O1 (58%). Observation of this stereospecific rearrangement supports prior arguments that substituents at C2 of the branched-chain aldofuranose reactant are located in a sterically accessible pocket of the putative dimolybdate-saccharide reactive complex during epimerization. This rearrangement provides a new and convenient route to 2-ketosugars glycosylated at the exocyclic C1 position.
ASJC Scopus subject areas
- Organic Chemistry