Nucleophilic displacement reactions of 5'-derivatised nucleosides in a vibration ball mill.
Nucleophilic displacement reactions of 5'-derivatised nucleosides in a vibration ball mill.
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DOI：
10.3762/bjoc.13.11
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发表时间：
2017
影响因子：
2.7
通讯作者：
Vyle JS
中科院分区：
文献类型：
--
作者：
Eguaogie O;Conlon PF;Ravalico F;Sweet JS;Elder TB;Conway LP;Lennon ME;Hodgson DR;Vyle JS
在氧化锆衬里的容器中进行振动球磨，在5到60分钟内，4-甲氧基苄基硫酸盐和核苷5′-卤化物或5′-tosylates之间进行了干净和定量的亲核位移反应。在这些条件下，没有观察到常见的核苷环化副产物（特别是嘌呤核苷）。在DMF的存在下，用硒氰酸钾对相同的5'-碘化物和5' -tosylate底物进行液体辅助研磨，在1到11小时的过程中以可变产量生产相应的5'-硒氰酸盐，从而避免了吸湿性四丁基铵盐的制备和使用。
Vibration ball-milling in a zirconia-lined vessel afforded clean and quantitative nucleophilic displacement reactions between 4-methoxybenzylthiolate salts and nucleoside 5′-halides or 5′-tosylates in five to 60 minutes. Under these conditions, commonly-encountered nucleoside cyclisation byproducts (especially of purine nucleosides) were not observed. Liquid-assisted grinding of the same 5'-iodide and 5′-tosylate substrates with potassium selenocyanate in the presence of DMF produced the corresponding 5′-selenocyanates in variable yields over the course of between one and eleven hours thereby avoiding the preparation and use of hygroscopic tetrabutylammonium salts.