Stereoselective synthesis of nicotinamide beta-riboside and nucleoside analogs

Bioorg Med Chem Lett. 2004 Sep 20;14(18):4655-8. doi: 10.1016/j.bmcl.2004.06.093.

Abstract

The beta-anomers of N-ribofuranosylnicotine-3-carboxamide (beta-NAR) and its nicotinic acid analog (beta-NaR) were obtained by stereoselective synthesis via glycosylation of the presilylated bases under Vorbruggen's protocol. A NAR analog, methylated in position 3 of the ribosylic moiety, is also reported.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Glycosylation
  • Niacinamide / analogs & derivatives*
  • Niacinamide / chemical synthesis*
  • Niacinamide / chemistry*
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry*
  • Pyridinium Compounds
  • Stereoisomerism

Substances

  • Nucleosides
  • Pyridinium Compounds
  • nicotinamide-beta-riboside
  • Niacinamide