手性催化剂环二肽类化合物的微波合成  

Synthesis of Chiral Catalyst of Cyclodipeptides under Microwave Irradiation

作　　者：唐子龙[1] 潘志[1] 罗娟[1] 刘汉文[1] 许栋梁[1] 谭凤姣[1] 

机构地区：[1]湖南科技大学化学化工学院

出　　处：《合成化学》2008年第5期542-545,553,共5页Chinese Journal of Synthetic Chemistry

基　　金：教育部留学回国人员科研启动基金资助项目;湖南省自然科学基金资助项目(06JJ50016);湖南省教育厅资助项目(07C288);湖南科技大学博士启动基金资助项目(E55105)

摘　　要：以L-苯丙氨酸或L-亮氨酸为起始原料,经过氨基保护和羧基酯化得到N-苄氧羰基-L-苯丙氨酸-对硝基苯酯(4a)或N-苄氧羰基-L-亮氨酸-对硝基苯酯(4b);4在三乙胺作用下与L-组氨酸甲酯盐酸盐缩合得到直链二肽N-苄氧羰基-L-苯丙氨酸-L-组氨酸甲酯(5a)或N-苄氧羰基-L-亮氨酸-L-组氨酸甲酯(5b);Pd/C催化5脱掉保护基后在微波辐射下,经环化反应合成了手性催化剂环二肽(6a或6b),其结构经1H NMR和IR表征。重点考察了由5合成6的反应条件。结果表明,以甲醇为溶剂,于65W辐射120min,6a和6b的产率分别达到90%和68%。A kind of chiral catalyst, cyclodipeptides（fa or 6b）, was synthesized from straight-chain dipeptides（5a or 5b） by deprotection using Pd/C as a catalyst and then cyclization under microwave irradiation. 5 was prepared in the presence of triethylamine by condensation between L-histidine methyl ester and N-carbobenzoxy-L-phenylalanine-p-nitrophenyl ester（4a） or N-carbobenzoxy-L-leucine-p-nitrophenyl ester（4b） which were synthesized from L-phenylalanine or L-leucine by amino protection and carboxyl esterification. The structures were characterized by 1H NMR and IR. The reaction conditions of synthesizing 6 from 5 were investigated. The experimental results showed that the yields of 6a and 6b reached 90% and 68%, respectively under 65 W for 120 min in methanol.

关 键 词：氨基酸 环二肽 微波辐射 合成 

分 类 号：O623.735[理学—有机化学]