STUDIES ON PHOSPHORYLATION .4. SELECTIVE PHOSPHORYLATION OF PRIMARY HYDROXYL GROUP IN NUCLEOSIDES
STUDIES ON PHOSPHORYLATION .4. SELECTIVE PHOSPHORYLATION OF PRIMARY HYDROXYL GROUP IN NUCLEOSIDES
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DOI：
10.1021/jo01258a004
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发表时间：
1969-01-01
影响因子：
3.6
通讯作者：
HONJO, M
中科院分区：
文献类型：
--
作者：
IMAI, KI;FUJII, S;HONJO, M
用焦磷酰氯在间甲酚或邻氯苯酚中直接磷酸化相应的未封闭核苷，高产率地合成了一些天然和人工合成的嘌呤和嘧啶核苷及其2‘-脱氧和2’-0-甲基衍生物的核苷5‘-磷酸。用类似的方法处理嘌呤、嘧啶、阿拉伯和葡萄糖核苷，以及马立菌素，均可使伯羟基选择性磷酸化，得到相应的磷酸盐。2-鸟苷和2‘-脱氧腺苷以较低的产率得到5’-磷酸。以9-J3-D-木糖呋喃糖腺嘌呤为原料合成了5‘-磷酸和3’，5‘-环磷酸。以乙腈、苯甲腈、乙酸乙酯、丙烯酸甲酯、苯甲酸乙酯和硝基苯为溶剂，在直接磷酰化反应中取得了满意的结果。
Nucleoside 5'-phosphates of a number of naturally occurring and synthetic purine and pyrimidine ribonu-cleosides and their 2'-deoxy and 2'-0-methyl derivatives were prepared in good yields by direct phosphorylation of their corresponding unblocked nucleosides with pyrophosphorylchloride in m-cresol or o-chlorophenol. Similar treatment of purine and pyrimidine arabino-andgluconucleosides, and aristeromycin resulted in the selective phosphorylation of the primary hydroxyl groups to give the corresponding phosphates.«-Guanosine and 2'-deoxyadenosine gave the 5'-phosphates in relatively low yield. The 5'-phosphate and 3', 5'-cyclic phosphate were obtained from 9-j3-D-xylofuranosyladenine. Acetonitrile, benzonitrile, ethyl acetate, methyl acrylate, ethyl benzoate and nitrobenzene, when used as solvents, gave satisfactory results in the direct phos-phorylation reaction.