(S)-1-tert-butyl 5-ethyl-2-(diallylamino)pentanedioate | 1428150-23-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-1-tert-butyl 5-ethyl-2-(diallylamino)pentanedioate
• 英文别名: 1-O-tert-butyl 5-O-ethyl (2S)-2-[bis(prop-2-enyl)amino]pentanedioate
• CAS: 1428150-23-5
• 化学式: C₁₇H₂₉NO₄
• 分子量: 311.422
• InChiKey: VDMCBPAXSUGFDP-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-1-tert-butyl 5-ethyl-2-(diallylamino)pentanedioate 在 sodium tetrahydroborate 、 四(三苯基膦)钯 、 甲酸 、 1,3-二甲基巴比妥酸 、 18-冠醚-6 、 三氧化硫吡啶 、 双(三甲基硅烷基)氨基钾 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 11.5h， 生成 (5S)-ethyl 5-((tert-butoxycarbonyl)amino)-2-hydroxycyclohex-3-ene carboxylate
  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
• 作为产物：
  描述：

  L-谷氨酸5乙脂 在 硫酸 、 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 38.0h， 生成 (S)-1-tert-butyl 5-ethyl-2-(diallylamino)pentanedioate
  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

文献信息

• JP6106452
  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.
• 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.