Acetalation of d-glucitol: 2,3:5,6-Di-O-isopropylidene-d-glucitol

János Kuszmann, Pál Sohár

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

The reaction of d-glucitol with acetone-zinc chloride gave a mixture of isopropylidene derivatives, from which the 2,3:5,6-diacetal (12) could be separated as its 1,4-dimesylate (13) or 1,4-ditosylate (14). The structure of 12 was proved by converting 14, via the 1-mono-iodide, into the known 1-deoxy-d-glucitol, and by mass-spectrometric investigation of the 1-deoxy-4-O-methyl diacetal. The terminally situated acetal group in 12 can be selectively hydrolyzed, and, on treatment with base, the 5,6-dihydroxy derivative obtained gives a d-galactitol 4,5-epoxide derivative.

Original languageEnglish
Pages (from-to)187-197
Number of pages11
JournalCarbohydrate Research
Volume74
Issue number1
DOIs
Publication statusPublished - Sep 1979

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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