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

E. Ősz, K. Czifrák, T. Deim, L. Szilágyi, A. Bényei, L. Somsák

Research output: Contribution to journalArticle

13 Citations (Scopus)

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

Fingerprint

Thiadiazoles
Dithionite
Hydrogen Sulfide
Methylene Chloride
Cyanides
Derivatives
Water
thioformamide
triethylamine
potassium bromate

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Preparation of 3,5-bis-(β-D-glycopyranosyl)-1,2,4-thiadiazoles from C-(β-D-glycopyranosyl)thioformamides. / Ősz, E.; Czifrák, K.; Deim, T.; Szilágyi, L.; Bényei, A.; Somsák, L.

In: Tetrahedron, Vol. 57, No. 25, 18.06.2001, p. 5429-5434.

Research output: Contribution to journalArticle

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AU - Ősz, E.

AU - Czifrák, K.

AU - Deim, T.

AU - Szilágyi, L.

AU - Bényei, A.

AU - Somsák, L.

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