A convenient synthesis of 2'-deoxy-2-fluoroadenosine; a potential prodrug for suicide gene therapy.

Academic Article

Abstract

  • A convenient synthesis of 2'-deoxy-2-fluoro-adenosine (1) is described. Deaminative fluorination of 2-aminoadenosine (2) followed by silylation of the 3', 5'-hydroxyl groups gave the corresponding 2-fluoroadenosine derivative 4 in good yield. Thiocarbonylation of 4 to thiocarbonylimidazolyl derivative 5a followed by treatment with an excess of tris(trimethylsilyl)silane (TTMSS) and tert-butyl peroxide in toluene at 80 degrees C was found to affect an efficient deoxygenation to the corresponding 2'-deoxy derivative 6. Desilylation of 6 by Et4NF in CH3CN afforded 1 in high yield.
  • Published In

    Keywords

  • Adenosine, Deoxyadenosines, Genetic Therapy, Prodrugs
  • Digital Object Identifier (doi)

    Pubmed Id

  • 18251036
  • Authorlist

  • Hassan AE; Shortnacy-Fowler AT; Montgomery JA; Secrist JA
  • Start Page

  • 559
  • End Page

  • 565
  • Volume

  • 19
  • Issue

  • 3