在球磨机中合成新型焦磷硫代酸酯连接的二核苷帽类似物。
Synthesis of novel pyrophosphorothiolate-linked dinucleoside cap analogues in a ball mill.
作者信息
Eguaogie Olga, Cooke Leonie A, Martin Patricia M L, Ravalico Francesco, Conway Louis P, Hodgson David R W, Law Christopher J, Vyle Joseph S
机构信息
School of Chemistry and Chemical Engineering, Queen's University Belfast, David Keir Building, Stranmillis Road, Belfast BT9 5AG, UK.
出版信息
Org Biomol Chem. 2016 Jan 28;14(4):1201-5. doi: 10.1039/c5ob02061a. Epub 2015 Nov 13.
Michaelis-Arbuzov reactions of S-aryl disulfide derivatives of 3'-thiothymidine or 5'-thioadenosine with tris(trimethylsilyl) phosphite proceeded in high yields to the corresponding phosphorothiolate monoesters. Subsequent hydrolytic desilylation and phosphate coupling were effected in one-pot using liquid-assisted grinding in a vibration ball mill. Novel 3',5'- and 5',5'-pyrophosphorothiolate-linked dinucleoside cap analogues were thereby prepared.
3'-硫代胸苷或5'-硫代腺苷的S-芳基二硫化物衍生物与亚磷酸三（三甲基硅基）酯的迈克尔is-阿尔布佐夫反应以高产率生成相应的硫代磷酸单酯。随后，使用振动球磨机中的液体辅助研磨在一锅法中进行水解去硅基化和磷酸偶联。由此制备了新型的3'，5'-和5'，5'-焦磷酸硫代磷酸酯连接的二核苷帽类似物。
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