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有机化学
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有机化学 ›› 2005, Vol. 25 ›› Issue (04): 438-441. 上一篇    下一篇

研究简报

克拉霉素的合成新方法

梁建华，姚国伟*   

  1. (北京理工大学生命科学与技术学院 北京 100081)
  • 收稿日期:2004-07-15 修回日期:2004-09-12 发布日期:2005-03-30
  • 通讯作者: 姚国伟

An Improvement for the Synthesis of Clarithromycin

LIANG Jian-Hua,YAO Guo-Wei*   

  1. (School of Life Science and Technology, Beijing Institute of Technology, Beijing 100081)
  • Received:2004-07-15 Revised:2004-09-12 Published:2005-03-30
  • Contact: YAO Guo-Wei

PDF

2810

被引次数

17

以醚化剂1-乙氧基环己烯和硅烷化试剂1,1,1,3,3,3-六甲基二硅氨烷为保护试剂, 采用醚化-硅烷化保护法制备了克拉霉素. 以红霉素A肟为原料计算, 经肟羟基醚化、2',4"-OH硅烷化、6-OH选择性甲基化、脱保护至克拉霉素, 四步反应总收率为49.5%.

关键词: 克拉霉素, 醚化, 区域选择性, 硅烷化

2',4"-O-bis(trimethylsilyl)erythromycin A 9-O-(1-ethoxycyclohexyl)oxime was prepared for the regioselective methylation by using 1-ethoxycyclohexene as etherification agents and 1,1,1,3,3,3-hexamethyldisilazane as silylation reagents. Four successive reactions from erythromycin A oxime to clarithromycin were operated in the form of one-pot protection (including etherification and silylation), regioselective methylation and one-pot deprotection with overall yield 49.5%.

Key words: clarithromycin, silylation, regioselectivity, etherification