Syntheses of novel glycosylidene-spiro-heterocycles related to hydantocidin

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17 Citations (Scopus)

Abstract

Reaction of 2,3,4,6-tetra-O-acetyl-1-bromo-1-deoxy-β-D- galactopyranosyl cyanide (4) with thiocyanate ions results in the formation of both anomers of per-O-acetylated 1-deoxy-1-thiocyanato-D-galactopyranosyl cyanides (5a and 5b). The thiocyanate group in these products is resistant to isomerization into isothiocyanate even at elevated temperatures. The X-ray structure of 5a is consistent with the operation of an exo-anomeric effect for the thiocyanate group. Compounds 5a and 5b react with hydrogen sulfide under mild conditions to yield galactopyranosylidene-spiro-thiazolidine (8) and -thiazoline (9, 12, and 13) derivatives.

Original languageEnglish
Pages (from-to)2419-2430
Number of pages12
JournalTetrahedron
Volume55
Issue number8
DOIs
Publication statusPublished - Feb 19 1999

Keywords

  • Carbohydrates
  • Spiro compounds
  • Thiazolidines
  • Thiazolines

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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