2-[4-[[(2R,3R,4R,5R,8R,9S,10S,11R,12R)-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-5-ethyl-2,4,8,10,12,14-hexamethyl-3,4-bis(2-methylpropanoyloxy)-7-oxo-6,15-dioxabicyclo[10.2.1]pentadec-1(14)-en-9-yl]oxymethyl]triazol-1-yl]acetic acid | 959903-52-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[4-[[(2R,3R,4R,5R,8R,9S,10S,11R,12R)-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-5-ethyl-2,4,8,10,12,14-hexamethyl-3,4-bis(2-methylpropanoyloxy)-7-oxo-6,15-dioxabicyclo[10.2.1]pentadec-1(14)-en-9-yl]oxymethyl]triazol-1-yl]acetic acid
• CAS: 959903-52-7
• 化学式: C₄₂H₆₈N₄O₁₃
• 分子量: 837.021
• InChiKey: LDEUYAJDECJLHC-BKCYNRKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  59
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  207
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  3-de-O-cladinosyl-11,12-di-O-iso-butyryl-3-O-propargyl-8,9-anhydroerythromycin 、 疊氮乙酸 在 copper(I) sulfate 、 铜 、 copper(II) sulfate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 36.0h， 以96%的产率得到2-[4-[[(2R,3R,4R,5R,8R,9S,10S,11R,12R)-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-5-ethyl-2,4,8,10,12,14-hexamethyl-3,4-bis(2-methylpropanoyloxy)-7-oxo-6,15-dioxabicyclo[10.2.1]pentadec-1(14)-en-9-yl]oxymethyl]triazol-1-yl]acetic acid
  参考文献：
  名称：

  Design and synthesis via click chemistry of 8,9-anhydroerythromycin A 6,9-hemiketal analogues with anti-MRSA and -VRE activity

  摘要：

  An erythromycin analogue, 11,12-di-O-iso-butyryl-8,9-anhydroerythromycin A 6,9-hemiketal (1b), was found to be a potential anti-MRSA and anti-VRE agent. The use of copper catalyzed azide-acetylene cycloaddition, and click chemistry, readily provided 10 types of triazole analogues of 1b in good to nearly quantitative yield. Among the library, 5b exhibited activity against MRSA and VRE bacterial strains, representing more than twice the potency of 1b. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.08.068

文献信息

• Design and synthesis via click chemistry of 8,9-anhydroerythromycin A 6,9-hemiketal analogues with anti-MRSA and -VRE activity
  作者：Akihiro Sugawara、Toshiaki Sunazuka、Tomoyasu Hirose、Kenichiro Nagai、Yukie Yamaguchi、Hideaki Hanaki、K. Barry Sharpless、Satoshi Ōmura

  DOI：10.1016/j.bmcl.2007.08.068

  日期：2007.11

  An erythromycin analogue, 11,12-di-O-iso-butyryl-8,9-anhydroerythromycin A 6,9-hemiketal (1b), was found to be a potential anti-MRSA and anti-VRE agent. The use of copper catalyzed azide-acetylene cycloaddition, and click chemistry, readily provided 10 types of triazole analogues of 1b in good to nearly quantitative yield. Among the library, 5b exhibited activity against MRSA and VRE bacterial strains, representing more than twice the potency of 1b. (C) 2007 Elsevier Ltd. All rights reserved.