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

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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

Keywords

  • C-nucleosides
  • conformational study
  • unsaturated tiazofurin analogues

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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