Improved chemical syntheses of 5,6-dihydro-5-fluorouracil

J Org Chem. 2007 Oct 26;72(22):8573-6. doi: 10.1021/jo071255z. Epub 2007 Sep 27.

Abstract

5,6-dihydro-5-fluorouracil (5-DHFU) is a metabolite of the chemotherapy drug 5-fluorouracil (5-FU) of importance for biological studies. 5-DHFU has been prepared by enzymatic reduction of 5-FU and in very low yield by hydrogenation of 5-FU; however, a practical chemical synthesis is not available. Facile racemic syntheses of 5-DHFU from 5-FU or uracil, using p-methoxybenzyl protecting groups followed by L-Selectride reduction, are reported.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Fluorouracil / analogs & derivatives*
  • Fluorouracil / chemical synthesis
  • Fluorouracil / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • 5-fluorodihydrouracil
  • Fluorouracil