Preparation of the 2'-deoxynucleosides of 2,6-diaminopurine and isoguanine by direct glycosylation

J Org Chem. 2010 Mar 5;75(5):1360-5. doi: 10.1021/jo902616s.

Abstract

The purine nucleoside 2,6-diaminopurine-2'-deoxyriboside is prepared by the direct glycosylation of the 2,6-bis(tetramethylsuccinimide) derivative of the parent purine heterocycle 4 with 2-deoxy-3,5-di-O-(p-toluoyl)-alpha-D-erythro-pentofuranosyl chloride 5 using the sodium salt method. 2'-Deoxyisoguanosine is prepared from 2,6-diaminopurine by a five-step procedure. The purine heterocycle isoguanine is prepared by selective diazotization of 2,6-diaminopurine and then converted to the N9-trityl derivative to increase solubility. After silylation of the O(2)-carbonyl with TMSCl, the N(6)-amino group is protected as the tetramethylsuccinimide (M(4)SI). The O(2)-carbonyl is protected as the DPC derivative, and the trityl group is removed. The resulting product is glycosylated in good yield to generate fully protected 2'-deoxyisoguanosine.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • 2-Aminopurine / analogs & derivatives*
  • 2-Aminopurine / chemical synthesis
  • 2-Aminopurine / chemistry
  • Adenosine
  • Glycosylation
  • Guanine / chemical synthesis*
  • Guanine / chemistry
  • Guanosine / chemical synthesis*
  • Guanosine / chemistry
  • Molecular Structure
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry
  • Purine Nucleosides / chemical synthesis*
  • Purine Nucleosides / chemistry
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Nucleosides
  • Purine Nucleosides
  • Guanosine
  • isoguanosine
  • 2-Aminopurine
  • 2,6-diaminopurine
  • Guanine
  • isoguanine
  • Adenosine