Synthesis of 1,6-thioanhydro-D-glucitol

J. Kuszmann, P. Sohár

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Treatment of 2,4-O-benzylidene-1,6-di-O-tosyl-D-glucitol (1) with potassium thiolbenzoate afforded the 6-S-benzoyl compound 2 and its 5-benzoate 4, the structure of which was proved chemically. When 1 was acetylated and then treated with the thiolate, the acetylated 6-S-benzoyl compound 19 was obtained in good yield in addition to some 1,6-di-S-benzoyl derivative 21. Treatment of 19 with acetic anhydride-acetic acid-sulfuric acid afforded 2,3,4,5-tetra-O-acetyl-6-S-acetyl-1-O-tosyl-D-glucitol (26), which was converted by sodium methoxide into a mixture of 1,5-anhydro-6-thio-D-glucitol (28) and 1,6-thioanhydro-D-glucitol (29). These two compounds were isolated as their acetates (30 and 31) by column chromatography, or by converting 28 into its S-trityl derivative (32).

Original languageEnglish
Pages (from-to)23-32
Number of pages10
JournalCarbohydrate Research
Volume48
Issue number1
DOIs
Publication statusPublished - 1976

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Sorbitol
Derivatives
Column chromatography
Benzoates
Acetic Acid
Methanol
Chromatography
Potassium
Acetates

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

Synthesis of 1,6-thioanhydro-D-glucitol. / Kuszmann, J.; Sohár, P.

In: Carbohydrate Research, Vol. 48, No. 1, 1976, p. 23-32.

Research output: Contribution to journalArticle

Kuszmann, J. ; Sohár, P. / Synthesis of 1,6-thioanhydro-D-glucitol. In: Carbohydrate Research. 1976 ; Vol. 48, No. 1. pp. 23-32.
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