diethyl (4R)-4-[bis(prop-2-enyl)amino]hept-2-ynedioate | 1428150-17-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: diethyl (4R)-4-[bis(prop-2-enyl)amino]hept-2-ynedioate
• CAS: 1428150-17-7
• 化学式: C₁₇H₂₅NO₄
• 分子量: 307.39
• InChiKey: ZKVSBPGQNYEHMY-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-氧代丁酸乙基酯 、 二烯丙基胺 、 丙炔酸乙酯 在 copper(ll) bromide 、 2,6-二[(4S)-4-苯基-2-恶唑啉基]吡啶 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以59%的产率得到
  参考文献：
  名称：

  Two Approaches toward the Formal Total Synthesis of Oseltamivir Phosphate (Tamiflu): Catalytic Enantioselective Three-Component Reaction Strategy and l-Glutamic Acid Strategy

  摘要：

  Two independent formal total syntheses of oseltamivir phosphate were successfully achieved: the first utilized a copper-catalyzed asymmetric three-component reaction strategy, and the second utilized L-glutamic acid gamma-ester as a chiral source to install the correct stereochemistry. Both strategies used Dieckmann condensation to construct a six-membered ring core, after which manipulation of the functional groups and protecting groups accessed Corey's intermediate for the synthesis of oseltamivir phosphate. While the first synthesis was accomplished via four purification steps in 25.7% overall yield, albeit with moderate optical purity (76% ee), the second strategy achieved the synthesis via six purification steps in 19.8% overall yield with perfect enantiocontrol.

  DOI：

  10.1021/jo400360j

文献信息

• EP2684866
  申请人：——

  公开号：——

  公开（公告）日：——
• Two Approaches toward the Formal Total Synthesis of Oseltamivir Phosphate (Tamiflu): Catalytic Enantioselective Three-Component Reaction Strategy and <scp>l</scp>-Glutamic Acid Strategy
  作者：Kaliyamoorthy Alagiri、Makoto Furutachi、Kenzo Yamatsugu、Naoya Kumagai、Takumi Watanabe、Masakatsu Shibasaki

  DOI：10.1021/jo400360j

  日期：2013.4.19

  Two independent formal total syntheses of oseltamivir phosphate were successfully achieved: the first utilized a copper-catalyzed asymmetric three-component reaction strategy, and the second utilized L-glutamic acid gamma-ester as a chiral source to install the correct stereochemistry. Both strategies used Dieckmann condensation to construct a six-membered ring core, after which manipulation of the functional groups and protecting groups accessed Corey's intermediate for the synthesis of oseltamivir phosphate. While the first synthesis was accomplished via four purification steps in 25.7% overall yield, albeit with moderate optical purity (76% ee), the second strategy achieved the synthesis via six purification steps in 19.8% overall yield with perfect enantiocontrol.