]Hexitol derivatives containing a 1,4-oxathiane ring

J. Kuszmann, P. Sohár

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

The synthesis of 2,5-anhydro-3-O-methylsulfonyl-6-thio-1,4-thioanhydro-D-galactitol (4; type A structure) and 2,5-anhydro-3,4-di-O-methylsulfonyl-1,6-thioanhydro-D-glucitol (10, type B structure), starting from 2,5-anhydro-1,6-dibromo-1,6-dideoxy-3,4-di-O-methylsulfonyl-D-glucitol (1) is described. The 4-O-methyl-sulfonyl group of 10 can be displaced by nucleophiles with retention of configuration. In this reaction, a cyclic sulfonium intermediate 21 is involved, which, depending on the nucleophilicity of the anion, leads to different ratios of type A and B compounds. Introduction of a three-membered ring into the 3,4-position of type B compounds yielded tricyclic derivatives of allitol.

Original languageEnglish
Pages (from-to)157-168
Number of pages12
JournalCarbohydrate Research
Volume27
Issue number1
DOIs
Publication statusPublished - 1973

Fingerprint

Sorbitol
Galactitol
Derivatives
Nucleophiles
Anions
hexitol
oxathiane
allitol

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

]Hexitol derivatives containing a 1,4-oxathiane ring. / Kuszmann, J.; Sohár, P.

In: Carbohydrate Research, Vol. 27, No. 1, 1973, p. 157-168.

Research output: Contribution to journalArticle

Kuszmann, J. ; Sohár, P. / ]Hexitol derivatives containing a 1,4-oxathiane ring. In: Carbohydrate Research. 1973 ; Vol. 27, No. 1. pp. 157-168.
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