O6-(benzotriazol-1-yl)inosine derivatives for C6 modification of purine nucleosides

Curr Protoc Nucleic Acid Chem. 2009 Mar:Chapter 1:Unit 1.22. doi: 10.1002/0471142700.nc0122s36.

Abstract

A new class of reactive nucleosides, O(6)-(benzotriazol-1-yl) derivatives of inosine and 2'-deoxyinosine, have been developed via reaction of silyl-protected or unprotected inosine and 2'-deoxyinosine with 1H-benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP). Alternatively, the silyl-protected O(6)-(benzotriazol-1-yl) derivatives can be synthesized via reaction of protected inosine and 2'-deoxyinosine with triphenylphosphine/iodine/1-hydroxybenzotriazole. These new O(6)-(benzotriazol-1-yl) inosine derivatives are excellent reagents for the synthesis of other nucleoside analogues via S(N)Ar reaction with a range of nucleophiles.

MeSH terms

  • Inosine / analogs & derivatives*
  • Inosine / chemistry
  • Organophosphorus Compounds / chemistry
  • Purine Nucleosides / chemistry*

Substances

  • Organophosphorus Compounds
  • Purine Nucleosides
  • benzotriazol-1-yloxy-tris(dimethylamino)phosphonium
  • Inosine
  • deoxyinosine