Stereoselective cyclopropanation in the synthesis of 3'-deoxy-3'-C-hydroxymethyl-2',3'-methylene-uridine

Org Lett. 2014 Sep 19;16(18):4878-80. doi: 10.1021/ol502383c. Epub 2014 Sep 11.

Abstract

The synthesis of the novel 2',3'-cyclopropane nucleoside 3'-deoxy-3'-C-hydroxymethyl-2',3'-methylene-uridine is described. Stereoselective construction of the cyclopropane ring was achieved via Simmons-Smith cyclopropanation of a benzyl protected silyl enol ether, which was itself derived from 1,2-O-isopropylidene-α-D-xylofuranose.

MeSH terms

  • Cyclopropanes / chemistry*
  • Molecular Structure
  • Monosaccharides / chemistry
  • Stereoisomerism
  • Uridine* / analogs & derivatives
  • Uridine* / chemical synthesis
  • Uridine* / chemistry
  • Uridine* / pharmacology

Substances

  • 1,2-isopropylidene-alpha-D-xylofuranose
  • 3'-deoxy-3'-C-hydroxymethyl-2',3'-methylene-uridine
  • Cyclopropanes
  • Monosaccharides
  • cyclopropane
  • Uridine