Acetalation of 1,6-anhydro-1(6)-thio-D-glucitol

János Kuszmann, Pál Sohár, Gyula Horváth

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Acetalation of 1,6-anhydro-1(6)-thio-D-glucitol (1a) with acetone, formaldehyde, or benzaldehyde afforded 2,3:4,5-diacetals (2a, 2b, and 2c) whose structure, after desulfurization, was proved by mass spectrometry. Upon partial hydrolysis of 2a, one of the isopropylidene groups was split off, and the other migrated to O-3,O-4 to give 4b. In 4b, in the stable conformation, OH-2 occupies an equatorial position, whereas OH-5 is axially oriented. Accordingly, OH-2 reacts faster than OH-5 on methylation of 4b, giving 4e. Hydrolysis of the isopropylidene group of the 2,5-di-O-methyl derivative 4d and subsequent mesylation afforded the corresponding 3,4-di-O-mesyl compound 1c, which showed significant ulcerostatic activity.

Original languageEnglish
Pages (from-to)45-52
Number of pages8
JournalCarbohydrate Research
Volume50
Issue number1
DOIs
Publication statusPublished - Aug 1976

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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