Polymer-supported reagents for methylphosphorylation and phosphorylation of carbohydrates

Bioorg Med Chem Lett. 2002 Jul 22;12(14):1863-6. doi: 10.1016/s0960-894x(02)00266-4.

Abstract

Two polymer-supported reagents for methylphosphorylation and phosphorylation of carbohydrates have been developed. p-Hydroxybenzyl alcohol and beta-mercaptoethanol were immobilized on cross-linked divinylbenzene-polystyrene copolymer and conjugated with methyl N,N-diisopropylchlorophosphoramidite. Carbohydrates were reacted with polymer-bound phosphitylating reagents. Further oxidation, with or without the methoxy group deprotection, and cleavage yielded methylphosphorylated or phosphorylated carbohydrates, respectively.

MeSH terms

  • Benzyl Alcohols / chemistry
  • Carbohydrates / chemistry*
  • Chemistry, Organic / methods
  • Hydrocarbons, Chlorinated / chemistry
  • Mercaptoethanol / chemistry
  • Organophosphates / chemical synthesis
  • Organophosphorus Compounds / chemistry
  • Oxidation-Reduction
  • Phosphorylation
  • Polymers / chemistry*
  • Polystyrenes / chemistry
  • Styrene / chemistry

Substances

  • Benzyl Alcohols
  • Carbohydrates
  • Hydrocarbons, Chlorinated
  • Organophosphates
  • Organophosphorus Compounds
  • Polymers
  • Polystyrenes
  • phosphoramidite
  • 4-hydroxybenzyl alcohol
  • Styrene
  • Mercaptoethanol