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2′,4″-O-双(三甲基硅)-6-O-甲基红霉素A9-O-(1-甲氧基环己基)肟的区域选择性合成机理及其晶体结构

Regioselective Synthesis Mechanism and Crystal Structure of 2′,4″-O-Bis(trimethylsilyl)-6-O-methylerythromycin A 9-O-(1-methoxycyclohexyl) oxime

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【作者】 梁建华姚国伟曹志凌甘强单春燕

【Author】 LIANG Jian-Hua, YAO Guo-Wei, CAO Zhi-Ling, GAN Qiang, SHAN Chun-Yan(School of Life Science and Technology, Beijing Institute of Technology , Beijing 100081, China)

【机构】 北京理工大学生命科学与技术学院北京理工大学生命科学与技术学院 北京100081北京100081

【Abstract】 2′,4″-O-Bis(trimethylsilyl) 6-O-methylerythromycin A 9-O-(1-methoxycyclohexyl) oxime was regioselectively synthesized and characterized and its crystal structure was determined by the single crystal X-ray structure analysis. The crystal belonged to tetragonal system with I4 space group and a=b=2.9720(4) nm, c=1.4939(3) nm, V=13.195(4) nm3, Z=8, R=0.0587, wR=0.1263, S=1.004 for 11526 unique reflections. The crystal structure shows that the attack of methylation reagents was blocked by 9-oxime ether as result, a hydrogen bond formed between 11-OH and nitrogen of 9-oxime, and the attack of methylation reagents was blocked by 9-oxime ether, whereas the orientation of 6-OCH3 was located in the cave surrounded by several rings so that 6-OH was unique one to be exposed to methylation reagents. However, the congestion around 11-OH was loosened, which resulted from the orientation of protective group so that much 6,11-O-dimethyl product was yielded. Additionally, the crystal structure of 2′,4″-O-bis(trimethylsilyl) erythromycin A 9-O-(1-methoxy-1-methylethyl) oxime was first disclosed as a comparison.

【关键词】 大环内酯区域选择性晶体结构
【Key words】 MacrolideRegioselectivityCrystal structure
【基金】 国家自然科学基金(批准号:20602002);北京理工大学基础研究基金(批准号:200506B4223)资助
  • 【文献出处】 高等学校化学学报 ,Chemical Journal of Chinese Universities , 编辑部邮箱 ,2007年03期
  • 【分类号】TQ465
  • 【被引频次】1
  • 【下载频次】186
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