Thiazole C-nucleosides. III. Synthesis of pyranose analogues of tiazofurin

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Abstract

A large-scale synthesis of 3,4,5-tri-0-acetyl-2,6-anhydro-L-mannono-and-D-gulonothioamides (5, 6) has been achieved from the corresponding nitriles. The Hantzsch reaction of (5) or (6) with ethyl bromopyruvate afforded the expected thiazoles (7.8) only in a low yield along with furan derivatives (9-11), the formation of which is rationalized by an acid-catalysed rearrangement-elimination process. The some Hantzsch reaction in the presence of barium carbonate yielded hydroxythiazolines (16,17). Attempted dehydration of (16) or (17) with trifluoroacetic anhydride or trifluoroacetic anhydride/pyridine resulted in the formation of pent-1′-enopyranosylthiazoles (18-20). Deprotected thioamides (24,25) furnished with ethyl bromopyruvate thiazoles (27,28). The obtained thiazole esters (7,8, 18-20. 27,28) were transformed into new tiazofurin analogues (12, 13, 21- 23).

Original languageEnglish
Pages (from-to)5539-5548
Number of pages10
JournalTetrahedron
Volume47
Issue number29
DOIs
Publication statusPublished - júl. 15 1991

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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