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有机化学
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有机化学 ›› 2009, Vol. 29 ›› Issue (04): 621-628. 上一篇    下一篇

研究论文

3-羟基克拉霉素和2′-乙酰基-3-氧代克拉霉素的合成与晶体结构

李玉川; 张立敏; 杨 翠; 张慧娟; 庞思平*; 赵信岐   

  1. (a北京理工大学生命科学与技术学院 北京 100081)
    (b北京理工大学材料科学与工程学院 北京 100081)
  • 收稿日期:2008-09-18 修回日期:2009-01-20 发布日期:2009-04-20
  • 通讯作者: 庞思平

Synthesis and Crystal Structure of 3-Hydroxyclarithromycin and 2′-Acetyl-3-oxo-clarithromycin

Li, Yuchuan ; Zhang, Limin; Yang, Cui ; Zhang, Huijuan ; Pang, Siping*;
Zhao, Xinqi
  

  1. (aSchool of Life Science and Technology, Beijing Institute of Technology, Beijing 100081)
    (bSchool of Material Science and Engineering, Beijing Institute of Technology, Beijing 100081)
  • Received:2008-09-18 Revised:2009-01-20 Published:2009-04-20
  • Contact: Pang, Siping

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克拉霉素在不同条件下水解, 分别生成3-羟基克拉霉素(2)和3-羟基-8,9,10,11-二脱水-9,12-半缩酮克拉霉素(3), 用乙酸酐保护2的C(2’)-OH得到2′-乙酰基-3-羟基克拉霉素(4), 用N-氯代琥珀酰亚胺(NCS)氧化4的C(3)—OH合成了2’-乙酰基-3-氧代克拉霉素(5), 采用MS, IR, 1H NMR, 13C NMR等对这些化合物进行了表征. 用X射线单晶衍射法测定了化合物2和5的晶体结构, 其均属于正交晶系, P212121 空间群. 化合物2的晶胞参数a＝1.3657(3) nm, b＝1.4783(3) nm, c＝1.6510(3) nm, Z＝4, V＝3.3332(12) nm3, Dc＝1.175 g/cm3, F(000)＝1288, μ＝0.087 mm－1; 化合物5的晶胞参数 a＝1.5124(3) nm, b＝1.5247(3) nm, c＝1.5288(3) nm, Z＝4, V＝3.5254(12) nm3, Dc＝1.187 g/cm3, F(000)＝1368.0, μ＝0.088 mm－1.

关键词: 克拉霉素, 合成, 晶体结构

Clarithromycin was hydrolyzed in different conditions to form 3-hydroxyclarithromycin (2) and 3-hydroxy-8,9,10,11-dehydrous-9,12-hemiketal clarithromycin (3) respectively, then C(2’)-OH of 2 was protected with an acetyl group to yield 2’-acetyl-3-hydroxyclarithromycin (4), C(3)-OH of 4 was then oxi-dized by N-chlorosuccinimide (NCS) to yield 2’-acetyl-3-oxo-clarithromycin (5), and their structures were characterized by MS, IR, 1H NMR and 13C NMR techniques. The crystal structures of 2 and 5 were deter-mined by X-ray single crystal diffraction analysis, which belong to orthorhombic system with space group P212121 and a＝13.657(3) nm, b＝14.783(3) nm, c＝16.510(3) nm, Z＝4, V＝3333.2(12) nm3, Dc＝1.175 g/cm3, F(000)＝1288, μ＝0.087 mm－1 (compound 2); a＝15.124(3) nm, b＝15.247(3) nm, c＝15.288(3) nm, Z＝4, V＝3525.4(12) nm3, Dc＝1.187 g/cm3, F(000)＝1368.0, and μ＝0.088 mm－1 (compound 5).

Key words: clarithromycin, synthesis, crystal structure