(S)-1-tert-butyl 5-ethyl 2-aminopentanedioate | 91255-02-6

• 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-aminopentanedioate
• 英文别名: L-Glutamic acid, 1-(1,1-dimethylethyl) 5-ethyl ester；1-O-tert-butyl 5-O-ethyl (2S)-2-aminopentanedioate
• CAS: 91255-02-6
• 化学式: C₁₁H₂₁NO₄
• 分子量: 231.292
• InChiKey: HZUJIPYKLAUVCX-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  78.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-1-tert-butyl 5-ethyl 2-aminopentanedioate 在 盐酸 、 碳酸氢钠 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 、 甲苯 为溶剂， 反应 32.75h， 生成
  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：

  醋酸叔丁酯 、 L-谷氨酸5乙脂 在 硫酸 作用下， 反应 18.0h， 以62%的产率得到(S)-1-tert-butyl 5-ethyl 2-aminopentanedioate
  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

• Glutamate aggrecanase inhibitors
  申请人：Sum Phaik-Eng

  公开号：US20070043066A1

  公开（公告）日：2007-02-22

  The present invention relates to modulators of metalloproteinase activity.

  本发明涉及金属蛋白酶活性调节剂。
• GLUTAMATE AGGRECANASE INHIBITORS
  申请人：Sum Phaik-Eng

  公开号：US20100010012A1

  公开（公告）日：2010-01-14

  The present invention relates to modulators of metalloproteinase activity.

  本发明涉及金属蛋白酶活性调节剂。
• 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：——
• US7553873B2
  申请人：——

  公开号：US7553873B2

  公开（公告）日：2009-06-30