Generation and Reactivity of an Unstabilized Carbohydrate Phosphorane

Academic Article


  • Generation of the ylide of methyl 5-deoxy-2,3-O-isopropylidene-5-(triphenylphosphonio)-β-d-ribofuranoside iodide (2a) is described. Treatment of the ylide with aldehydes affords good yields of olefinic products of the α-l-lyxo configuration, resulting from epimerization of the ylide prior to reaction. Ketones do not react cleanly with the ylide. Addition of a proton source to the ylide under appropriate conditions allows the formation of good yields of a self-condensation product 14. © 1977, American Chemical Society. All rights reserved.
  • Published In

    Digital Object Identifier (doi)

    Pubmed Id

  • 11137267
  • Author List

  • Secrist JA; Wu SR
  • Start Page

  • 4084
  • End Page

  • 4088
  • Volume

  • 42
  • Issue

  • 25