使用关键中间体碳环AICA-核苷合成碳环嘌呤核苷。

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

作者信息

Marumoto R, Taniyama Y, Fukuda T

机构信息

Biotechnology Laboratories, Takeda Chemical Industries Ltd, Osaka, Japan.

出版信息

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.

摘要

用1N氢氧化钠/乙醇水溶液处理碳环N1-甲氧基甲基肌苷和2'-脱氧肌苷，分别得到碳环5-氨基-4-咪唑甲酰胺核糖苷和-2'-脱氧核糖苷。两种有用的关键中间体与苯甲酰异硫氰酸酯反应，高产率地得到相应的5-(N-异硫代氨基甲酰基)衍生物。异硫代氨基甲酰基甲基化，然后用氢氧化钠处理，导致嘌呤环闭合（鸟嘌呤、异鸟嘌呤和黄苷）反应。

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