Versatile synthesis of rare nucleotide furanoses

Org Lett. 2007 Dec 6;9(25):5227-30. doi: 10.1021/ol702392x. Epub 2007 Nov 13.

Abstract

Direct activation of unprotected thioimidoyl furanosides yielded in only one step and few minutes a panel of rare uridine 5'-diphospho-furanoses. Diastereoselectivity of the reaction was tightly connected with reaction time, temperature, and nature of the furanosyl donor. This approach was totally selective since no ring expansion from the initial five-membered ring to the more stable pyranose form was observed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Imidoesters / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Nucleotides / chemical synthesis*
  • Nucleotides / chemistry
  • Phosphorylation
  • Sulfhydryl Compounds / chemistry
  • Uridine / chemistry
  • Uridine Diphosphate / chemistry

Substances

  • Imidoesters
  • Nucleotides
  • Sulfhydryl Compounds
  • Uridine Diphosphate
  • Uridine