C-C Bond Formation: Synthesis of C5 Substituted Pyrimidine and C8 Substituted Purine Nucleosides Using Water Soluble Pd-imidate Complex

Curr Protoc Nucleic Acid Chem. 2016 Jun 1:65:1.37.1-1.37.15. doi: 10.1002/cpnc.1.

Abstract

The synthesis of a highly efficient, water soluble [Pd(Sacc)2 (TPA)2 ] complex for C-C bond formation is described. Additionally, application of the [Pd(Sacc)2 (TPA)2 ] complex for Suzuki-Miyaura arylation of all four nucleosides (5-iodo-2'-deoxyuridine [5-IdU], 5-iodo-2'-deoxycytidine [5-IdC], 8-bromo-2'-deoxyadenosine, and 8-bromo-2'-deoxyguanosine) with various aryl/heteroaryl boronic acids in plain water under milder conditions is demonstrated. © 2016 by John Wiley & Sons, Inc.

Keywords: Suzuki-Miyaura cross-coupling; base-modified nucleosides; nucleotides; palladium catalyst.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chemistry Techniques, Synthetic
  • Deoxyadenosines / chemical synthesis
  • Deoxyadenosines / chemistry
  • Deoxyguanosine / analogs & derivatives
  • Deoxyguanosine / chemical synthesis
  • Deoxyguanosine / chemistry
  • Organophosphorus Compounds / chemistry
  • Palladium / chemistry
  • Purine Nucleosides / chemical synthesis*
  • Purine Nucleosides / chemistry
  • Pyrimidines / chemical synthesis*
  • Pyrimidines / chemistry
  • Solubility
  • Water

Substances

  • 8-bromo-2'-deoxyguanosine
  • Deoxyadenosines
  • Organophosphorus Compounds
  • Purine Nucleosides
  • Pyrimidines
  • phosphoramidite
  • Water
  • 8-bromo-2'-deoxyadenosine
  • Palladium
  • Deoxyguanosine