(S)-ethyl 4-(diallylamino)-5-hydroxypentanoate | 1428150-25-7

• 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: (S)-ethyl 4-(diallylamino)-5-hydroxypentanoate
• 英文别名: ethyl (4S)-4-[bis(prop-2-enyl)amino]-5-hydroxypentanoate
• CAS: 1428150-25-7
• 化学式: C₁₃H₂₃NO₃
• 分子量: 241.331
• InChiKey: OZYCGKIPAFENCI-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-ethyl 4-(diallylamino)-5-hydroxypentanoate 在 N-甲基咪唑 、 2,2'-联吡啶 、 sodium tetrahydroborate 、 四(三苯基膦)钯 、 1,3-二甲基巴比妥酸 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 2,2,6,6-四甲基哌啶氧化物 、 sodium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 sodium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 7.67h， 生成 (S)-ethyl 5-((tert-butoxycarbonyl)amino)cyclohexa-1,3-dienecarboxylate
  参考文献：
  名称：

  Chromatography-free synthesis of Corey's intermediate for Tamiflu

  摘要：

  Column chromatography-free stereoselective synthesis of Corey's intermediate for Tamiflu (oseltamivir phosphate) was achieved, starting from L-glutamic acid gamma-ethyl ester. The reagents and solvents used in the reaction scheme are industrially tractable, rendering the synthesis a potential starting point for process research. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.09.081
• 作为产物：
  描述：

  L-谷氨酸5乙脂 在 sodium tetrahydroborate 、 甲酸 、 高氯酸 、 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 反应 69.75h， 生成 (S)-ethyl 4-(diallylamino)-5-hydroxypentanoate
  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

• 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.
• JP6106452
  申请人：——

  公开号：——

  公开（公告）日：——
• Chromatography-free synthesis of Corey's intermediate for Tamiflu
  作者：Makoto Furutachi、Naoya Kumagai、Takumi Watanabe、Masakatsu Shibasaki

  DOI：10.1016/j.tet.2014.09.081

  日期：2014.11

  Column chromatography-free stereoselective synthesis of Corey's intermediate for Tamiflu (oseltamivir phosphate) was achieved, starting from L-glutamic acid gamma-ethyl ester. The reagents and solvents used in the reaction scheme are industrially tractable, rendering the synthesis a potential starting point for process research. (C) 2014 Elsevier Ltd. All rights reserved.