3-(N-9-腺嘌呤)丙氨酸和3-(N-1-尿嘧啶)丙氨酸的合成与表征.pdf

SYNTHE SISAND CHARACTERIZATION OF3一(N一9一ADENINE)ALANINE AND 3一(N一1一URACIL)ALANINE ADissertation Submitted to theGraduate School ofHenan Normal University inPartialFulfillment oftheRequirements fortheDegree of Master ofScience By Yan Wenjuan Supervisor: Cunshuan Qianyi May 2013 摘要研究发现,许多核苷类似物是重要的工业原料、药物前体和药物,研发这类化合物一直是研究热点。为此,)丙氨酸和3.() 丙氨酸,为研究它们的作用和应用前景提供材料。首先,合成了N.(叔丁氧羰基).。在这个反应过程中,分别尝试了氯代和碘代两种卤代方式,通过对产物的产率和纯度进行分析比较,最终确定氯代效率最高。接着,将N.(叔丁氧羰基).,.()丙氨酸甲酯进行脱氨基保护反应,再进行分离和纯化,得到产物3.()丙氨酸甲酯。同时, 对反应条件进行了优化,筛选出最佳反应条件,并探讨了碱、温度、反应时间、反应底物投料比和溶剂使用量对反应产率的影响。类似地,针对N.(叔丁氧羰基).,也进行了最佳反应条件的筛选,并从碱、温度、反应时间、反应底物投料比和溶剂使用量方面讨论其对反应产率的影响,)丙氨酸甲酯。下一步进行3.()丙氨酸甲酯和 3.()丙氨酸甲酯的脱甲基保护和获得目的产物实验。整个实验过程操作简便,反应条件温和,产率较高,后处理简单,该合成方法为合成核苷类似物提供了新思路。产物3.()丙氨酸甲酯和3.()丙氨酸甲酯的结构得到质谱,核磁共振氢谱,核磁共振碳谱和红外光谱的表征和验证。产物3.(. 腺嘌呤))丙氨酸甲酯丰富了核苷类化合物的种类,为后期检测它们的生物活性奠定了基础。关键词:核苷类似物,腺嘌呤,尿嘧啶,3.()丙氨酸,3.()丙氨酸 ABSTRACT Researches show that many nucleoside analogues are important industrial raw materials, prodrugs and the development ofnucleoside analogues has been research this dissertation,the nucleoside analogues 3—04—9-adenine)alanine and3-04-1-uracil)alanine were designed for synthesis and further study oftheir functions and application. Firstly,the 3-halogenation ofthe N-(tert-butoxycarbonyl)·L-serine methyl ester was launched. parison ofthe yield and purity,chlorination ismore efficient than ,the chlorinated product methyl 2-(tert-butoxycarbonyl)··3..chloropropanoate was used with adenine give 2-(tert-butoxycarbonyl)-3-04—9-adenine)alanine methyl deamination reaction of2-(tert-butoxycarbonyl)·3-04-9-adenine)alanine methyl product 3-04-9-adenine)alanine methyl was the same time,the reaction conditions were optimized,and the in