Synthesis of C-β-D-Ribofuranosyl Derivatives with a Highly Functionalized Two-Carbon Unit. Conversion to Certain Blocked Thiazole C-Nucleosides

Academic Article

Abstract

  • Condensation of halo ylides 17-20 with 2,3-0-isopropylidene-5-0-trityl-D-ribofuranose (13) produced exclusively the C-nucleoside precursors 3, 4, 6, and 7, all with the β configuration. With 17 and 18, compounds postulated to be the ring-opened derivatives 27 and 28 were the major products formed initially. Treatment of 27 and 28 with a catalytic amount of DBU converted them rapidly to 6 and 7. Treatment of 3, 4, 6, and 7 with sodium methoxide did not result in the formation of any a isomers. Reduction of halo esters 6 and 7 with diisobutylaluminum hydride at low temperature afforded halo aldehydes 9 and 10. Treatment of halo ketones 3 and 4 with various thioamides produced the blocked thiazole C-nucleosides 35-39. © 1983, American Chemical Society. All rights reserved.
  • Digital Object Identifier (doi)

    Pubmed Id

  • 11261762
  • Author List

  • Clingerman MC; Secrist JA
  • Start Page

  • 3141
  • End Page

  • 3145
  • Volume

  • 48
  • Issue

  • 19