Thiazole C-nucleosides IV. An entry to pent-1′-enopyranosylthiazole derivatives

L. Kovács, P. Herczegh, G. Batta, István Farkas

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Starting from ethyl 2-(3′,4′-di-O-acetyl-2′-deoxy-L-erythro-or -D-threo-pent-1′-enopyranosyl)thiazole-4-carboxylate (1, 2) the synthesis of variously functionalized pent-1′-enopyranosylthiazoles (4-11, 15-20) was carried out with different O-, C-, S-, N-, and H-nucleophiles in the presence of Lewis acids. The regio- and stereoselective reactions proceeded with the Lewis acid-mediated formation of a carbocation (I) and the stereochemistry of the incoming nucleophile was determined by the neighbouring 4′-acetoxy group. However, with trimethylsilyl cyanide a 2′,3′-unsaturated 1′-C-cyano derivative (26) was formed. The configuration and conformation of prepared unsaturated compounds was thoroughly studied and the presence of a conformational equilibrium 4H55H4 was deduced.

Original languageEnglish
Pages (from-to)5549-5560
Number of pages12
JournalTetrahedron
Volume47
Issue number29
DOIs
Publication statusPublished - Jul 15 1991

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Thiazoles
Lewis Acids
Nucleophiles
Nucleosides
Unsaturated compounds
Derivatives
Stereochemistry
Conformations
trimethylsilyl cyanide

Keywords

  • C-nucleosides
  • conformational study
  • unsaturated tiazofurin analogues

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Thiazole C-nucleosides IV. An entry to pent-1′-enopyranosylthiazole derivatives. / Kovács, L.; Herczegh, P.; Batta, G.; Farkas, István.

In: Tetrahedron, Vol. 47, No. 29, 15.07.1991, p. 5549-5560.

Research output: Contribution to journalArticle

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AU - Farkas, István

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