Uracil Nucleosides with Reactive Group at C5 Position: 5-(1-Halo-2-sulfonylvinyl)uridine Analogues

Org Lett. 2016 Mar 18;18(6):1418-21. doi: 10.1021/acs.orglett.6b00346. Epub 2016 Mar 2.

Abstract

The transition-metal-catalyzed or radical-mediated halosulfonylation of 5-ethynyluridine provided (E)-(1-halo-2-tosylvinyl)uridines. These (β-halo)vinyl sulfones undergo efficient stereoselective addition-elimination with amines or thiols to provide Z-β-aminovinyl or E-β-thiovinyl sulfones tethered to the C5 position of the uracil ring.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Molecular Structure
  • Nucleosides
  • Structure-Activity Relationship
  • Sulfones / chemical synthesis
  • Sulfones / chemistry*
  • Uracil / analogs & derivatives
  • Uridine* / analogs & derivatives
  • Uridine* / chemical synthesis
  • Uridine* / chemistry

Substances

  • Nucleosides
  • Sulfones
  • Uracil
  • divinyl sulfone
  • Uridine