Synthesis of sugar nucleotides by application of phosphoramidites

J Org Chem. 2008 Dec 5;73(23):9458-60. doi: 10.1021/jo802021t.

Abstract

A new method for the construction of pyrophosphates is reported based on the coupling of a sugar phosphate and a nucleoside phosphoramidite. The in situ formed phosphate-phosphite intermediate was subsequently oxidized with tBuOOH. Three UDP-N-acetylglucosamine derivatives were prepared using this one-pot procedure in good yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylglucosamine / chemistry
  • Carbohydrates / chemistry*
  • Chemistry, Organic / methods
  • Magnetic Resonance Spectroscopy / methods
  • Models, Chemical
  • Nucleosides / chemistry
  • Nucleotides / chemistry
  • Organophosphorus Compounds / chemistry*
  • Phosphates / chemistry
  • Phosphites / chemistry
  • Uridine Diphosphate / chemistry

Substances

  • Carbohydrates
  • Nucleosides
  • Nucleotides
  • Organophosphorus Compounds
  • Phosphates
  • Phosphites
  • phosphoramidite
  • Uridine Diphosphate
  • Acetylglucosamine