双吖丙啶-羧酸光交联分子的合成研究

Synthesis of diazidinecarboxylic acid photocrosslinking molecule

本研究报道一种双吖丙啶-羧酸类光交联分子3-[3-(3-丁炔-1-基)-3H-双吖丙啶-3-基]丙酸(1)的合成方法。以乙酰乙酸乙酯(2)和溴代丙炔(3)为原料,依次经历亲核取代反应、缩酮保护、酯还原、脱乙二醇保护、双吖丙啶化、羟基保护、氰基取代、氰基水解等8步反应,合成得到目标化合物(1),中间体及产物结构经1 HNMR及ESI-MS表征。并对关键步骤的反应条件进行考察,确定适宜的合成反应条件。

A synthetic method for 3-(3-(but-3-yn-1-yl)-3H-diazirin-3-yl)propanoic acid(1)as a diazirine-carboxylic acid pho-tocrosslinking molecule was reported.Using Ethyl 3-oxobutanoate(2)and 3-bromoprop-1-yne(3)as starting materials,it underwent nucleophilic substitution reaction,ketal protection,ester reduction,ethylene glycol protection,diacridification,hydroxyl protection,cyano substitution,cyano hydrolysis,etc.The target compound(1)and intermediates were characterized by^(1)H NMR and ESI-MS.The reaction conditions of the key steps were investigated and the suitable synthetic reaction conditions were determined.