(αS,3S,5S)-5-(methoxycarbonyl)-1-(1,1-dimethylethoxy)carbonyl-α-[[(1,1-dimethylethoxy)carbonyl]amino]-2-oxo-3-pyrrolidineacetic acid methyl ester | 1242161-31-4

• 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: (αS,3S,5S)-5-(methoxycarbonyl)-1-(1,1-dimethylethoxy)carbonyl-α-[[(1,1-dimethylethoxy)carbonyl]amino]-2-oxo-3-pyrrolidineacetic acid methyl ester
• 英文别名: methyl (2S,4S,6S)-N-tert-butoxycarbonyl-4-(methoxycarbonyl-N-tert-butoxycarbonylaminomethyl)pyroglutamate；1-O-tert-butyl 2-O-methyl (2S,4S)-4-[(1S)-2-methoxy-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-oxoethyl]-5-oxopyrrolidine-1,2-dicarboxylate
• CAS: 1242161-31-4
• 化学式: C₁₉H₃₀N₂O₉
• 分子量: 430.455
• InChiKey: OVBMIHORJAUAKY-SRVKXCTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (αS,3S,5S)-5-(methoxycarbonyl)-1-(1,1-dimethylethoxy)carbonyl-α-[[(1,1-dimethylethoxy)carbonyl]amino]-2-oxo-3-pyrrolidineacetic acid methyl ester 在 盐酸 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 26.0h， 以99%的产率得到(αS,3S,5S)-α-amino-5-carboxy-2-oxo-3-pyrrolidineacetic acid
  参考文献：
  名称：

  Total synthesis of penmacric acids via an intermolecular radical addition reaction

  摘要：

  The total syntheses of penmacric acid and its three stereoisomers were accomplished through the intermolecular radical addition reaction of the 4-pyrrolidyl radical derived from trans-4-hydroxy-L-proline. Furthermore, 1',3-diepi-penmacric acid was synthesized stereoselectively via double stereoinduction in the radical reaction. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.006
• 作为产物：
  描述：

  Boc-L-焦谷氨酸甲酯 、 2-(N-tert-butoxycarbonylimino)acetic acid methyl ester 在 四氯化钛 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以62.3%的产率得到(αS,3S,5S)-5-(methoxycarbonyl)-1-(1,1-dimethylethoxy)carbonyl-α-[[(1,1-dimethylethoxy)carbonyl]amino]-2-oxo-3-pyrrolidineacetic acid methyl ester
  参考文献：
  名称：

  A short formal synthesis of three epimers of penmacric acid

  摘要：

  An extremely short formal synthesis of three epimers of penmacric acid is accomplished starting from pyroglutamate in one or two steps. Stereochemical outcome in the reaction of Li and Ti enolates of pyroglutamate with imines is found to be dependent on both chelation and steric factors. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.05.102

文献信息

• Total synthesis of penmacric acids via an intermolecular radical addition reaction
  作者：Masafumi Ueda、Ayako Ono、Dai Nakao、Kenji Matsuno、Takeaki Naito、Okiko Miyata

  DOI：10.1016/j.tet.2013.06.006

  日期：2013.8

  The total syntheses of penmacric acid and its three stereoisomers were accomplished through the intermolecular radical addition reaction of the 4-pyrrolidyl radical derived from trans-4-hydroxy-L-proline. Furthermore, 1',3-diepi-penmacric acid was synthesized stereoselectively via double stereoinduction in the radical reaction. (C) 2013 Elsevier Ltd. All rights reserved.
• A short formal synthesis of three epimers of penmacric acid
  作者：Dimpy Sikriwal、Ruchir Kant、Prakas R. Maulik、Dinesh K. Dikshit

  DOI：10.1016/j.tet.2010.05.102

  日期：2010.8

  An extremely short formal synthesis of three epimers of penmacric acid is accomplished starting from pyroglutamate in one or two steps. Stereochemical outcome in the reaction of Li and Ti enolates of pyroglutamate with imines is found to be dependent on both chelation and steric factors. (C) 2010 Elsevier Ltd. All rights reserved.