Photochemistry on soluble polymer supports: synthesis of nucleosides

Org Lett. 2002 Dec 12;4(25):4415-7. doi: 10.1021/ol026881r.

Abstract

[reaction: see text] A new soluble polymer support synthesis of nucleosides is described. The photochemical ring expansion of cyclobutanones in the presence of poly(ethylene glycol) (PEG) results in polymer-supported ribosides. These photoadducts can be cleaved from the polymer under Vorbrüggen coupling conditions with TMS-protected purines and pyrimidines to give ribonucleosides. The method has been extended to include modified PEGs with dendritic end-groups in order to improve the loading levels for these coupling reactions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclobutanes / chemistry
  • Ketones / chemistry
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry*
  • Photochemistry
  • Polyethylene Glycols / chemistry
  • Polymers / chemistry*
  • Ribonucleosides / chemical synthesis
  • Ribonucleosides / chemistry

Substances

  • Cyclobutanes
  • Ketones
  • Nucleosides
  • Polymers
  • Ribonucleosides
  • Polyethylene Glycols