6-O-methyl-4″-O-(2-benzoyl-6-deoxy-3-dimethylamino-β-D-desosaminyl)erythromycin A 11,12-cyclic carbonate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-methyl-4″-O-(2-benzoyl-6-deoxy-3-dimethylamino-β-D-desosaminyl)erythromycin A 11,12-cyclic carbonate
• 英文别名: [(2S,3R,4S,5S,6R)-4-(dimethylamino)-2-[(2S,3S,4R,6R)-6-[[(1R,2R,5R,6S,7S,8R,9R,11R,13R,14R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-9-methoxy-1,5,7,9,11,13-hexamethyl-4,12,16-trioxo-3,15,17-trioxabicyclo[12.3.0]heptadecan-6-yl]oxy]-4-methoxy-2,4-dimethyloxan-3-yl]oxy-5-hydroxy-6-methyloxan-3-yl] benzoate
• 化学式: C₅₄H₈₆N₂O₁₈
• 分子量: 1051.28
• InChiKey: FZLYERJKZVZHFP-ZUWPVQLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  74
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  226
• 氢给体数：
  2
• 氢受体数：
  20

反应信息

• 作为产物：
  描述：

  克拉霉素 在 吡啶 、 三乙基硅基三氟甲磺酸酯 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 44.0h， 生成 6-O-methyl-4″-O-(2-benzoyl-6-deoxy-3-dimethylamino-β-D-desosaminyl)erythromycin A 11,12-cyclic carbonate
  参考文献：
  名称：

  Synthesis of 4″-O-desosaminyl clarithromycin derivatives and their anti-bacterial activities

  摘要：

  A series of new 4"-O-desosaminyl clarithromycin derivatives were designed and synthesized. The efficient synthesis routes of 6-deoxy-desosamine donors 8 and 11 were developed and the methodology of glycosylation of clarithromycin 4"-OH with desosamine was studied. The activities of the target compounds were tested against a series of macrolide-sensitive and macrolide-resistant pathogens. Some of them showed activities against macrolide sensitive pathogens, and compounds 19 and 22 displayed significant improvement of activities against sensitive pathogens and two strains of MRSE, which verified the importance of desosamine in the interaction of macrolide and its receptor, and offered valuable information of the SAR of macrolide 4"-OH derivatives. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.083

文献信息

• Synthesis of 4″-O-desosaminyl clarithromycin derivatives and their anti-bacterial activities
  作者：Di Zhu、Yanpeng Xu、Yi Liu、Xiaozhuo Chen、Zhehui Zhao、Pingsheng Lei

  DOI：10.1016/j.bmcl.2013.09.083

  日期：2013.12

  A series of new 4"-O-desosaminyl clarithromycin derivatives were designed and synthesized. The efficient synthesis routes of 6-deoxy-desosamine donors 8 and 11 were developed and the methodology of glycosylation of clarithromycin 4"-OH with desosamine was studied. The activities of the target compounds were tested against a series of macrolide-sensitive and macrolide-resistant pathogens. Some of them showed activities against macrolide sensitive pathogens, and compounds 19 and 22 displayed significant improvement of activities against sensitive pathogens and two strains of MRSE, which verified the importance of desosamine in the interaction of macrolide and its receptor, and offered valuable information of the SAR of macrolide 4"-OH derivatives. (C) 2013 Elsevier Ltd. All rights reserved.