A disaccharide rearrangement catalyzed by molybdate anion in aqueous solution

Qingquan Wu, Qingfeng Pan, Shikai Zhao, Heidi Imker, Anthony S. Serianni

Research output: Contribution to journalArticle

Abstract

(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.

Original languageEnglish (US)
Pages (from-to)3081-3084
Number of pages4
JournalJournal of Organic Chemistry
Volume72
Issue number8
DOIs
StatePublished - Apr 13 2007
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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