【作者】 曾凡云；

【导师】 朱为宏； 苏熠东；

【作者基本信息】 华东理工大学 ， 制药工程， 2011， 硕士

【摘要】 本论文主要采用了一种新的方法合成了对甲基苯丙氨酸,它是一种重要的非天然氨基酸。此氨基酸的合成,对于其它非天然氨基酸的合成也具有借鉴意义,尤其是其它取代的苯基或杂环取代的α-丙氨酸。针对目标产物,根据逆合成分析,结合相关的文献,比较了其它的路线,最终选择以对甲基苄氯和丙二酸二乙酯为起始原料,经过烷基化、水解、成环、氨解、酰胺降解、五步反应制得目标产物对甲基苯丙氨酸,总收率24-25%。该路线避免了传统路线中使用的含重金属的试剂或者剧毒化学品,所有原料都廉价易得,所有操作都没有过柱分离,操作简单,具有工业化规模生产的潜力。更多还原

【Abstract】 The dissertation is focused on the synthesis of an important unnatural amino acid p-methyl-phenylalanine. The synthetic route is very guidable to synthesize other unnatural amino acids, especially for other substituted phenyl or heterocylic substituted alpha alanines.Based on the chemical structure of p-methyl-phenylalanine, we utilized the disconnection method via retrosynthetic analysis to compare several possible routes as well as reaction conditions with the reported literatures. A novel possible route was proposed and established, starting from 1-(chloromethyl)-4-methyl benzene and diethyl malonate via alkylation, hydrolysis, cyclization, ammonation, Hofman degradation, with an overall yield of 24-25%. The synthetic route has several advantages, such as commercially available and cheap raw materials, no heavy metal reagents or highly poisonous chemicals involved. Moreover, all separation operations are not required to column chromatography, large potential to scale up for industrialization, promising to get independent intellectual property rights.更多还原