Synthesis of carbocyclic purine nucleosides using key intermediates, carbocyclic AICA-ribosides.
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.
Marumoto
R
R
Biotechnology Laboratories, Takeda Chemical Industries Ltd, Osaka, Japan.
Taniyama
Y
Y
Fukuda
T
T
D000620:Aminoimidazole Carboxamide / Q000031:analogs & derivatives; D007202:Indicators and Reagents; D008745:Methylation; D011684:Purine Nucleosides / Q000138:chemical synthesis*; D012263:Ribonucleosides
D007202:Indicators and Reagents; D011684:Purine Nucleosides; D012263:Ribonucleosides; D000620:Aminoimidazole Carboxamide; C011651:acadesine