Ketone exchange in a sugar bisacetal

Richard S. Glass, Shuan Kwoh, Eugene P. Oliveto

Research output: Contribution to journalArticle

2 Scopus citations

Abstract

An acid-catalyzed reaction of 2,3:4,6-di-O-isopropylidene-α-l-sorbofuranose with ketones resulted in replacement of the isopropylidene groups with alkylidene groups derived from the ketonic solvent. Kinetically controlled exchange occurs at the 4,6-position. Under equilibrium conditions exchange occurs at the 2,3- as well as the 4,6-position. Participation by the hydroxyl group at C-1 in the rate determining step of exchange at the 2,3-position could not be demonstrated.

Original languageEnglish (US)
Pages (from-to)181-189
Number of pages9
JournalCarbohydrate Research
Volume26
Issue number1
DOIs
StatePublished - Jan 1973

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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