Preparation of 3,5-bis-(β-D-glycopyranosyl)-1,2,4-thiadiazoles from C-(β-D-glycopyranosyl)thioformamides

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Abstract

Acylated C-glycopyranosyl thioformamides of D-gluco, D-galacto, and D-xylo configuration were obtained by treating the corresponding glycosyl cyanides with hydrogen sulfide in the presence of triethylamine. The thioformamides gave 3,5-bis-(β-D-glycopyranosyl)-1,2,4-thiadiazoles in reactions with potassium bromate and sodium dithionite in dichloromethane-water biphasic solvent mixture. Deprotected derivatives were prepared by Zemplén deacylation.

Original languageEnglish
Pages (from-to)5429-5434
Number of pages6
JournalTetrahedron
Volume57
Issue number25
DOIs
Publication statusPublished - Jun 18 2001

Keywords

  • 1,2,4-thiadiazole
  • Bromination
  • Carbohydrates
  • Oxidation
  • Thioamide

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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