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 language | English (US) |
|---|---|
| Pages (from-to) | 3081-3084 |
| Number of pages | 4 |
| Journal | Journal of Organic Chemistry |
| Volume | 72 |
| Issue number | 8 |
| DOIs | |
| State | Published - Apr 13 2007 |
| Externally published | Yes |
ASJC Scopus subject areas
- Organic Chemistry