Stereo-controlled C-C bond formation at the anomeric position of uracil nucleosides

Nucleic Acids Symp Ser. 1993:(29):31-2.

Abstract

Stereoselective synthesis of 1'-carbon-substituted uracil nucleosides has been achieved through face-selective bromo-pivaloyloxylation of a 1',2'-unsaturated derivative and successive SnCl4-promoted nucleophilic substitution with organosilicon reagents. This constitutes the first example of C-C bond formation at the anomeric position of nucleosides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbon / chemistry*
  • Nucleosides / chemistry*
  • Organosilicon Compounds / chemistry
  • Stereoisomerism
  • Uracil / chemistry*

Substances

  • Nucleosides
  • Organosilicon Compounds
  • Uracil
  • Carbon