((2R,3S,4S,5R,6S)-4-azido-6-(((1S,2S,3R,4S,6R)-4,6-diazido-3-(((2R,3R,5S,6R)-3-azido-6-(azidomethyl)-5-hydroxytetrahydro-2H-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)-3,5-dihydroxytetrahydro-2H-pyran-2-yl)methyl 2,4,6-triisopropylbenzenesulfonate | 1477468-26-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((2R,3S,4S,5R,6S)-4-azido-6-(((1S,2S,3R,4S,6R)-4,6-diazido-3-(((2R,3R,5S,6R)-3-azido-6-(azidomethyl)-5-hydroxytetrahydro-2H-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)-3,5-dihydroxytetrahydro-2H-pyran-2-yl)methyl 2,4,6-triisopropylbenzenesulfonate
• CAS: 1477468-26-0
• 化学式: C₃₃H₄₉N₁₅O₁₁S
• 分子量: 863.912
• InChiKey: IDPDTUHRALRUDA-HJDSPAIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.25
• 重原子数：
  60.0
• 可旋转键数：
  17.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  405.01
• 氢给体数：
  4.0
• 氢受体数：
  16.0

反应信息

• 作为产物：
  描述：

  2,4,6-三异丙基苯磺酰氯 、 penta-azidotobramycin 在 吡啶 作用下， 反应 18.0h， 以56%的产率得到((2R,3S,4S,5R,6S)-4-azido-6-(((1S,2S,3R,4S,6R)-4,6-diazido-3-(((2R,3R,5S,6R)-3-azido-6-(azidomethyl)-5-hydroxytetrahydro-2H-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)-3,5-dihydroxytetrahydro-2H-pyran-2-yl)methyl 2,4,6-triisopropylbenzenesulfonate
  参考文献：
  名称：

  Site-Selective Displacement of Tobramycin Hydroxyls for Preparation of Antimicrobial Cationic Amphiphiles

  摘要：

  A short site-selective strategy for the activation and derivatization of alcohols of the clinically important aminoglycoside tobramycin is reported. The choice of amine protecting group affected the site-selective conversion of secondary alcohols of tobramycin into leaving groups. Temperature-dependent, chemoselective sequential nucleophilic displacements resulted in hetero- and homodithioether tobramycin-based cationic amphiphiles that demonstrated marked antimicrobial activity and impressive membrane selectivity.

  DOI：

  10.1021/ol4030138