(9E)-4''-O-(allyloxycarbonyl)-N-demethylerythromycin A 9-(O-allyloxime) 2',3'-carbamate-11,12-carbonate | 1063590-45-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: (9E)-4''-O-(allyloxycarbonyl)-N-demethylerythromycin A 9-(O-allyloxime) 2',3'-carbamate-11,12-carbonate
• CAS: 1063590-45-3
• 化学式: C₄₅H₇₀N₂O₁₇
• 分子量: 911.054
• InChiKey: HEVBPXXMZURTPP-DCDSTDNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.83
• 重原子数：
  64.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  214.87
• 氢给体数：
  1.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  (9E)-4''-O-(allyloxycarbonyl)-N-demethylerythromycin A 9-(O-allyloxime) 2',3'-carbamate-11,12-carbonate 在 lithium thiopropiolate 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 反应 2.0h， 以79%的产率得到(9E)-N-demethylerythromycin A 9-(O-allyloxime) 2',3'-carbamate-11,12-carbonate
  参考文献：
  名称：

  Preparation and antibacterial activity of cyclic 2′,3′-carbamate derivatives of azithromycin

  摘要：

  In a study of the importance of a basic amino function in erythromycin derived antibiotics, N '-demethylazithromycin 2 ',3 '-carbamate-11, 12-carbonate has been prepared in six steps from (9E)-erythromycin A 9-oxime. Reactions with phosgene provided a cyclic carbonate from the vicinal 11,12-diol, and a cyclic 2 ',3 '-carbamate from the vicinal dimethylamino-alcohol moiety of the desosamine sugar. Further transformations provided N,N '-di(demethyl)azithromycin 2 ',3 '-carbamate-11, 12-carbonate N-methylated at position 9a. The activity of the oxime was reduced in comparison with the parent azithromycin. Hence the N,N-dimethylamino group in the desosamine sugar is important for good antibacterial activity. The course of the phosgene reactions has been verified by an X-ray analysis. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.10.013
• 作为产物：
  描述：

  、 烯丙醇 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.75h， 以9.33 g的产率得到(9E)-4''-O-(allyloxycarbonyl)-N-demethylerythromycin A 9-(O-allyloxime) 2',3'-carbamate-11,12-carbonate
  参考文献：
  名称：

  Preparation and antibacterial activity of cyclic 2′,3′-carbamate derivatives of azithromycin

  摘要：

  In a study of the importance of a basic amino function in erythromycin derived antibiotics, N '-demethylazithromycin 2 ',3 '-carbamate-11, 12-carbonate has been prepared in six steps from (9E)-erythromycin A 9-oxime. Reactions with phosgene provided a cyclic carbonate from the vicinal 11,12-diol, and a cyclic 2 ',3 '-carbamate from the vicinal dimethylamino-alcohol moiety of the desosamine sugar. Further transformations provided N,N '-di(demethyl)azithromycin 2 ',3 '-carbamate-11, 12-carbonate N-methylated at position 9a. The activity of the oxime was reduced in comparison with the parent azithromycin. Hence the N,N-dimethylamino group in the desosamine sugar is important for good antibacterial activity. The course of the phosgene reactions has been verified by an X-ray analysis. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.10.013