Synthesis, conformational analysis, and biological activity of C-thioribonucleosides related to tiazofurin.

@article{Franchetti2000SynthesisCA,
  title={Synthesis, conformational analysis, and biological activity of C-thioribonucleosides related to tiazofurin.},
  author={Palmarisa Franchetti and Stefano Marchetti and Loredana Cappellacci and Hiremagalur N. Jayaram and Joel A. Yalowitz and Barry M. Goldstein and J. L. Barascut and David Dukhan and J. L. Imbach and Mario Grifantini},
  journal={Journal of medicinal chemistry},
  year={2000},
  volume={43 7},
  pages={
          1264-70
        }
}
The syntheses of furanthiofurin [5beta-D-(4'-thioribofuranosyl)furan-3-carboxamide, 1] and thiophenthiofurin [5beta-D-(4'-thioribofuranosyl)thiophene-3-carboxamide, 2], two C-thioribonucleoside analogues of tiazofurin, are described. Direct trifluoroacetic acid-catalyzed C-glycosylation of ethyl furan-3-carboxylate with 1-O-acetyl-2,3,5-tri-O-benzyl-4-thio-D-ribofuranose gave 2- and 5-glycosylated regioisomers, as a mixture of alpha and beta anomers. Ethyl 5-(2,3,5-tri-O-benzyl)-beta-D-(4… Expand
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