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Synthesis of carbocyclic purine nucleosides using key intermediates, carbocyclic AICA-ribosides
R Marumoto1, Y Taniyama, T Fukuda
1Biotechnology Laboratories, Takeda Chemical Industries Ltd, Osaka, Japan.
Nucleic Acids Symposium Series
|January 1, 1987
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.