【作者】 马敏； 姚国伟； 邓玉林； 史颖；

【Author】 MA, Min YAO, Guo-Wei? DENG, Yu-Lin SHI, Ying (School of Life Science and Technology, Beijing Institute of Technology, Beijing, 100081)

【机构】 北京理工大学生命科学与技术学院；

【摘要】 目的:研究以水为溶剂一锅煮合成氮红霉素的绿色合成工艺;方法:以水为溶剂、红霉素肟为原料、甲磺酰氯为催化剂,在pH为7～8、温度为20℃的条件下进行贝克曼重排反应后,不分离产物,将温度降到-10℃后,直接加入NaBH4进行还原,得到氮红霉素硼酸酯,水解后得到氮红霉素;结果:以红霉素肟计,合成氮红霉素两步反应总产率为90%,纯度为88%。结论:该工艺减少了设备,避免了有机溶剂的使用,为阿奇霉素的绿色合成提供了可能。更多还原

【Abstract】 Objective: To develop a simple and environmental-friendly technique of preparing the 9-deoxo-9a-aza-9a- homoerythromycin A (AZA), which is the precursor of azithromycin. Method: Water is used as a solvent instead of acetone and methane sulfonyl chloriede as the activator, Beckmann rearrangement reaction of erythromycin A oxime occurs at 293 K and pH = 7~8. And then directly lower the temperature of reaction system to 263 K, add sodium borohydride and catalyzer into the system, and subsequently erythromycin 6,9--imino ether suffer reduction and hydrolyzation reactions ordinally. At last, AZA is obtained Results: Two successive reactions from erythromycin A oxime to AZA were operated in one pot with overall yield 90%. Conclusion: This enronmental-friendly one-pot process can simplify the synthesis and make full use of erythromycin A oxime, especially avoid the usage of some poisonous solvent.更多还原