Synthesis of carbocyclic purine nucleosides using key intermediates, carbocyclic AICA-ribosides

Nucleic Acids Symp Ser. 1987:(18):37-40.

Abstract

Treating carbocyclic N1-methoxymethy-inosine and 2'-deoxy-inosine with 1N-NaOH/aq.EtOH gave the carbocyclic 5-amino-4-imidazolecarboxamide-riboside and -2'-deoxyriboside respectively. Reaction of both useful key intermediates with PhCONCS afforded the corresponding 5-(N-isothiocarbamoyl) derivatives in high yield. Methylation of the isothiocarbamoyl groups, followed by treatment with NaOH led to the purine ring-closure (guanine, isoguanine, and xanthosine) reaction.

MeSH terms

  • Aminoimidazole Carboxamide / analogs & derivatives
  • Indicators and Reagents
  • Methylation
  • Purine Nucleosides / chemical synthesis*
  • Ribonucleosides

Substances

  • Indicators and Reagents
  • Purine Nucleosides
  • Ribonucleosides
  • Aminoimidazole Carboxamide
  • acadesine