Polymer-bound oxathiaphospholane: a solid-phase reagent for regioselective monothiophosphorylation and monophosphorylation of unprotected nucleosides and carbohydrates

Org Lett. 2005 May 12;7(10):1955-8. doi: 10.1021/ol050385w.

Abstract

Two polymers bound to N,N-diisopropylamino-1,3,2-oxathiaphospholane were reacted with unprotected carbohydrates and nucleosides in the presence of 1H-tetrazole, followed by oxidation with tert-butyl hydroperoxide or sulfurization with Beaucage's reagent. The 1,3,2-oxathiaphospholane ring-opening with 3-hydroxypropionitrile, followed by treatment with DBU, afforded the corresponding monophosphate and monothiophosphate derivatives, respectively, through the elimination of polymer-bound ethylene episulfide. Reactions using this strategy offer the advantages of high regioselectivity, monosubstitution, and facile isolation and recovery of products.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Carbohydrates / chemistry*
  • Indicators and Reagents
  • Nucleosides / chemistry*
  • Nucleotides / chemistry*
  • Polymers / chemistry*
  • Ribose / analogs & derivatives*
  • Ribose / chemistry
  • Stereoisomerism

Substances

  • Carbohydrates
  • Indicators and Reagents
  • Nucleosides
  • Nucleotides
  • Polymers
  • oxathiaphospholane
  • Ribose