Synthesis of Certain β-D-Ribofuranosyl Thiazole C-Nucleosides from a Versatile Precursor

Academic Article


  • A synthesis of the versatile C-nucleoside precursor 3, 6-anhydro-2-bromo-2-deoxy-4, 5-O-isopropylidene-7-O-trityl-D-a(Zo-heptose (lc) is described. Treatment of lc with various thiocarbamoyl-containing compounds (6) in hexamethylphosphoramide results in the formation of protected 2-substituted-5-C-ribosylthiazoles 7-9. Liberation of the nucleosides 10-12 is accomplished with either methanolic hydrogen chloride or aqueous formic acid. Complete 13C and NMR data are presented for all compounds. © 1979, American Chemical Society. All rights reserved.
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    Digital Object Identifier (doi)

    Author List

  • Cousineau TJ; Secrist JA
  • Start Page

  • 4351
  • End Page

  • 4358
  • Volume

  • 44
  • Issue

  • 24