Synthesis of 2-fluoro and 4-fluoro galactopyranosyl phosphonate analogues of UDP-Gal

Carbohydr Res. 2012 Oct 1:360:31-9. doi: 10.1016/j.carres.2012.07.015. Epub 2012 Aug 2.

Abstract

Two novel nonisosteric UDP-Gal analogues, (2-deoxy-2-fluoro- and 4-deoxy-4-fluoro-α-D-galactopyranosyl) phosphonoyl phosphates, were synthesized by optimized multistep procedures starting from 3,4,6-tri-O-benzyl-D-galactal and allyl 2,3,6-tri-O-benzyl-α-D-glucopyranoside, respectively. The key steps were a Michaelis-Arbuzov reaction of respective deoxy-fluoro-D-galactopyranosyl acetate with triethyl phosphite followed by a Moffatt-Khorana coupling reaction with UMP-morpholidate. The structure of all new compounds was confirmed by NMR and mass spectroscopies..

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Deoxyglucose / analogs & derivatives*
  • Deoxyglucose / chemical synthesis
  • Deoxyglucose / chemistry
  • Organophosphonates / chemical synthesis*
  • Organophosphonates / chemistry
  • Uridine Diphosphate Galactose / analogs & derivatives*
  • Uridine Diphosphate Galactose / chemical synthesis*
  • Uridine Diphosphate Galactose / chemistry

Substances

  • Organophosphonates
  • Uridine Diphosphate Galactose
  • Deoxyglucose