C-Glycosyl 1,2,4-triazoles: Synthesis of the 3-β-D-glucopyranosyl-1,5-disubstituted and 5-β-D-glucopyranosyl-1,3-disubstituted variants

Katalin E. Szabó, András Páhi, László Somsák

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Highly variable synthetic routes were elaborated toward trisubstituted C-glycopyranosyl 1,2,4-triazoles. N-Acyl-thioamide derivatives were obtained by acylation of O-perbenzoylated 2,6-anhydro-D-glycero-D-gulo-heptonothioamide by acid chlorides and of thioamides by O-perbenzoylated 2,6-anhydro-D-glycero-D-gulo-heptonoyl chloride. These precursors reacted with substituted hydrazines in a regioselective manner to yield 3-β-D-glucopyranosyl-1,5-disubstituted- and 5-β-D-glucopyranosyl-1,3-disubstituted-1,2,4-triazoles, respectively. Analogous N-acyl-2,6-anhydro-heptonamides failed to give the above triazoles with hydrazines. O-Deprotection of the C-glucosyl 1,2,4-triazoles by the Zemplén method furnished test compounds which showed no inhibition against rabbit muscle glycogen phosphorylase b.

Original languageEnglish
Pages (from-to)3810-3822
Number of pages13
JournalTetrahedron
Volume73
Issue number27-28
DOIs
Publication statusPublished - Jan 1 2017

    Fingerprint

Keywords

  • 1,2,4-Triazole
  • 2,6-Anhydro-aldonamide
  • 2,6-Anhydro-aldonothioamide
  • C-Glycosyl heterocycle

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this