【作者】 彭洪伟；

【导师】 白国义；

【作者基本信息】 河北大学 ， 有机化学， 2008， 硕士

【摘要】 7-氨基-3-乙烯基头孢烷酸(7-AVCA)是合成第三代头孢菌素头孢克肟和头孢地尼的重要起始原料。本文设计并成功建立了以GCLE为原料合成7-AVCA的路线,并对其工艺条件进行了优化,确定了合成7-AVCA的最佳条件：当n(GCLE):n(PPh3): n(NaI):n(HCHO):n(NaOH)为1.0：1.1：1.0：10.6：0.976时,3-乙烯基头孢菌素中间体3.1的收率为94.5%,产品的纯度为96.0%；当n(化合物3.1)：n(苯酚)为1.0：10.0,反应温度为60℃,反应时间为4h时,7-AVCA的收率为79.0%,产品的纯度为97.5%。在此基础上,以GCLE为起始原料和不同醛合成了一系列7-AVCA的类似物,包括乙醛类似物(7-APCA),水杨醛类似物3.4,邻香草醛类似物3.6。同时,设计并建立了由7-ACA为原料制备7-APCA的合成路线。更多还原

【Abstract】 7-Amino-3-vinylcephalosporanic acid (7-AVCA) is an important starting material for the synthesis of cefixime and cefdinir, the third-generation oral cephalosporins. The synthetic route of 7-AVCA from GCLE was designed and successfully established in the paper. The reaction condition were optimized and confirmed. The yield of 3-vinylcephem intermediate 3.1 is 94.5% with a purity of 96.0% while the ratio of n(GCLE):n(PPh3):n(NaI): n(HCHO):n(NaOH) is 1.0:1.1:1.0:10.6:0.976. The yield of 7-AVCA is 79.0% with a purity of 97.5% while the ratio of n(3-vinylcephem intermediate 3.1):n(phenol) is 1.0:10.0, the temperature is 60℃and the reaction time is 4 h in the deprotection process.A series of 7-AVCA analgues were also synthesized from GCLE and different aldehydes, including acetaldehyde analogue (7-APCA), salicylaldehyde analogue 3.4 and o-vanillin analogue 3.6. Moreover, a synthetic route of 7-APCA from 7-ACA was also designed and established.更多还原