(1S,2R,3S,4R,5S)-4-acetamido-5-(((benzyloxy)carbonyl)amino)-3-hydroxy-2-(pentan-3-yloxy)cyclohexane-1-carboxylic acid | 1184177-23-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2R,3S,4R,5S)-4-acetamido-5-(((benzyloxy)carbonyl)amino)-3-hydroxy-2-(pentan-3-yloxy)cyclohexane-1-carboxylic acid
• CAS: 1184177-23-8
• 化学式: C₂₂H₃₂N₂O₇
• 分子量: 436.505
• InChiKey: ILMVVDCZPKTQSG-UHZRXMQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  134.19
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  (3aR,4S,6S,7R,7aS)-7-acetamido-6-(((benzyloxy)carbonyl)amino)-2,2-diethylhexahydrobenzo[d][1,3]dioxole-4-carboxylic acid 在 boron fluoride-dimethyl sulfide complex 、 四氯化钛 作用下， 以40%的产率得到(1S,2R,3S,4R,5S)-4-acetamido-5-(((benzyloxy)carbonyl)amino)-3-hydroxy-2-(pentan-3-yloxy)cyclohexane-1-carboxylic acid
  参考文献：
  名称：

  An alternative synthesis of Tamiflu®: a synthetic challenge and the identification of a ruthenium-catalyzed dihydroxylation route

  摘要：

  Synthetic studies of Tamiflu (R) and the identification of a ruthenium-catalyzed dihydroxylation route are disclosed. This newly developed synthetic process circumvents the need for a Mitsunobu inversion step and the use of explosive reagents. This route, therefore, compares favorably to the previously developed synthetic process. (C) 2009 Elsevier Ltd. All rights reserved,

  DOI：

  10.1016/j.tet.2009.05.077