(2S,3R,4S,6R)-4-(((benzyloxy)carbonyl)(methyl)amino)-2-(((1S,2R,3R,6R,7S,8S,9R,10R,12R,14R)-3-ethyl-2,7-dihydroxy-10-methoxy-2,6,8,10,12,14-hexamethyl-5,13-dioxo-4,15-dioxabicyclo[12.1.0]pentadecan-9-yl)oxy)-6-methyltetrahydro-2H-pyran-3-yl acetate | 1428676-60-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (2S,3R,4S,6R)-4-(((benzyloxy)carbonyl)(methyl)amino)-2-(((1S,2R,3R,6R,7S,8S,9R,10R,12R,14R)-3-ethyl-2,7-dihydroxy-10-methoxy-2,6,8,10,12,14-hexamethyl-5,13-dioxo-4,15-dioxabicyclo[12.1.0]pentadecan-9-yl)oxy)-6-methyltetrahydro-2H-pyran-3-yl acetate
• CAS: 1428676-60-1
• 化学式: C₃₉H₅₉NO₁₃
• 分子量: 749.896
• InChiKey: AQIUADQTASLDCI-UJYKJMNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  53.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  179.89
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,6R)-4-(((benzyloxy)carbonyl)(methyl)amino)-2-(((1S,2R,3R,6R,7S,8S,9R,10R,12R,14R)-3-ethyl-2,7-dihydroxy-10-methoxy-2,6,8,10,12,14-hexamethyl-5,13-dioxo-4,15-dioxabicyclo[12.1.0]pentadecan-9-yl)oxy)-6-methyltetrahydro-2H-pyran-3-yl acetate 在 palladium on activated charcoal 、 氢气 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Synthesis and antibacterial activity of novel 10,11-epoxy acylide erythromycin derivatives

  摘要：

  A series of novel acylide derivatives have been synthesized from clarithromycin A via a facile procedure. The C-3 modifications involved replacing the natural C-3 cladinosyl group in clarithromycin core with different aryl-piperzine sidechain via chemical synthesis. Meanwhile a distinctive intermediate with 10,11-epoxy moiety was obtained. The structure and stereochemistry of this novel structure were confirmed via NMR and X-ray crystallography. Potential anti-bacterial activities against both Gram-positive and Gram-negative bacteria were reported. Because of existence of C10,11-epoxide, these derivatives can be used as intermediates for further structural modification. (C) 2013 Qi-Dong You. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2013.02.015
• 作为产物：
  描述：

  克拉霉素 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 碳酸氢钠 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 间氯过氧苯甲酸 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 83.0h， 生成 (2S,3R,4S,6R)-4-(((benzyloxy)carbonyl)(methyl)amino)-2-(((1S,2R,3R,6R,7S,8S,9R,10R,12R,14R)-3-ethyl-2,7-dihydroxy-10-methoxy-2,6,8,10,12,14-hexamethyl-5,13-dioxo-4,15-dioxabicyclo[12.1.0]pentadecan-9-yl)oxy)-6-methyltetrahydro-2H-pyran-3-yl acetate
  参考文献：
  名称：

  Synthesis and antibacterial activity of novel 10,11-epoxy acylide erythromycin derivatives

  摘要：

  A series of novel acylide derivatives have been synthesized from clarithromycin A via a facile procedure. The C-3 modifications involved replacing the natural C-3 cladinosyl group in clarithromycin core with different aryl-piperzine sidechain via chemical synthesis. Meanwhile a distinctive intermediate with 10,11-epoxy moiety was obtained. The structure and stereochemistry of this novel structure were confirmed via NMR and X-ray crystallography. Potential anti-bacterial activities against both Gram-positive and Gram-negative bacteria were reported. Because of existence of C10,11-epoxide, these derivatives can be used as intermediates for further structural modification. (C) 2013 Qi-Dong You. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2013.02.015