A highly facile and efficient one-step synthesis of N6-adenosine and N6-2'-deoxyadenosine derivatives

Org Lett. 2005 Dec 22;7(26):5877-80. doi: 10.1021/ol052424+.

Abstract

[reaction: see text] A highly facile and efficient one-step synthesis of N6-adenosine and N6-2'-deoxyadenosine derivatives has been developed. Treatment of inosine or 2'-deoxyinosine, without protection of sugar hydroxyl groups, with alkyl or arylamines, in the presence of BOP and DIPEA in DMF, led to the formation of N6-adenosine and N6-2'-deoxyadenosine derivatives in good to excellent yields. Carcinogenic polyaromatic hydrocarbon (PAH) N6-2'-deoxyadenosine adduct 10 and a rare DNA constituent 11 were thus synthesized directly from 2'-deoxyinosine both in 98% yield.

MeSH terms

  • Adenosine* / analogs & derivatives
  • Adenosine* / chemical synthesis
  • Adenosine* / chemistry
  • Combinatorial Chemistry Techniques*
  • Deoxyadenosines / chemical synthesis*
  • Molecular Structure

Substances

  • Deoxyadenosines
  • Adenosine