First synthesis of 4'-selenonucleosides showing unusual Southern conformation

Org Lett. 2008 Jan 17;10(2):209-12. doi: 10.1021/ol7025558. Epub 2007 Dec 19.

Abstract

The first synthesis of 4'-selenonucleosides was achieved using a Pummerer-type condensation as a key step. All stereoelectronic effects shown in 4'-oxonucleosides were overwhelmed by the size of selenium and steric interactions, driving the conformation to the C2'-endo/ C3'-exo twist (Southern) conformation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Models, Molecular
  • Molecular Structure
  • Nucleic Acid Conformation
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry
  • Organoselenium Compounds / chemical synthesis*
  • Organoselenium Compounds / chemistry

Substances

  • Nucleosides
  • Organoselenium Compounds