新型大环内酯类抗生素塞红霉素关键中间体的合成

Synthesis of the key intermediate of cethromycin(ABT-773) ,a novel ketolide

目的:合成新型大环内酯类抗生素ABT-773(cethromycin,塞红霉素)关键中间体并进行工艺改进。方法:3-(3-喹啉)-2(E)-丙烯-1-醇叔丁基碳酸酯以3-澳喹啉为原料经3步合成侧链,然后从红霉素A肟开始,经酯化、烃基化、去保护得到目标化合物。结果:经质谱、核磁共振氢谱确证,合成了ABT-773侧链和关键中间体,总收率达46％。结论:本工艺简单,成本低,收率高。

Objective: To synthesize the key intermediate of cethromycin(ABT-773) and improve the synthetic procedure. Methods:3-(3-quinoly)-2-propynl-l-ol t-butyl dicarbonate was synthesized from 3-bromoquinoline in three steps;the key intermediate of ABT-773 was synthesized throughesterification,alkylenation and deprotection. Results: The key intermediate of ABT-773 was synthesized successfully and the chemical structure of the target compound was confirmed by MS,1H-NMR, total yield was 46 % . Conclusion: This improved procedure was convenient to industry with low consumption.