4-Acetoxy-2-acetylamino-2-ethoxycarbonyl-pentanedioic acid diethyl ester | 871269-34-0

• 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: 4-Acetoxy-2-acetylamino-2-ethoxycarbonyl-pentanedioic acid diethyl ester
• 英文别名: Triethyl 1-acetamido-3-acetyloxypropane-1,1,3-tricarboxylate
• CAS: 871269-34-0
• 化学式: C₁₆H₂₅NO₉
• 分子量: 375.376
• InChiKey: WXLZCNAHDYQILP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  26
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-Acetoxy-2-acetylamino-2-ethoxycarbonyl-pentanedioic acid diethyl ester 在 盐酸 、 碳酸氢钠 作用下， 以 吡啶 、 水 为溶剂， 反应 80.0h， 生成 4-Benzyloxycarbonylamino-2-hydroxy-4-(4-methoxy-benzylcarbamoyl)-butyric acid
  参考文献：
  名称：

  Synthesis of Racemic cis-5-Hydroxy-3-phthalimidoglutarimide. A Metabolite of Thalidomide Isolated from Human Plasma

  摘要：

  A synthesis of the glutarimide-derived metabolite of thalidomide, 5'-hydroxythalidomide (2), is described. The synthesis employed the lactone derivative of N-benzyloxycarbonyl (CBZ)-protected 4-hydroxyglutamic acid 12, which is prepared by a de novo route from diethyl acetamidomalonate. The reaction of 12 with 4-methoxybenzylamine gave the corresponding isoglutamine, which then provided the key CBZ-protected N-PMB-glutarimide 14 after dehydration. Deprotection of both the CBZ and PMB groups followed by phthalimidation and deacetylation of the 3-amino-5-acetoxyglutarimide 16 afforded 2.

  DOI：

  10.1021/jo0514772
• 作为产物：
  描述：

  ethyl α-acetoxy-β-chlorolactate 、 乙酰氨基丙二酸二乙酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.83h， 以88%的产率得到4-Acetoxy-2-acetylamino-2-ethoxycarbonyl-pentanedioic acid diethyl ester
  参考文献：
  名称：

  Synthesis of Racemic cis-5-Hydroxy-3-phthalimidoglutarimide. A Metabolite of Thalidomide Isolated from Human Plasma

  摘要：

  A synthesis of the glutarimide-derived metabolite of thalidomide, 5'-hydroxythalidomide (2), is described. The synthesis employed the lactone derivative of N-benzyloxycarbonyl (CBZ)-protected 4-hydroxyglutamic acid 12, which is prepared by a de novo route from diethyl acetamidomalonate. The reaction of 12 with 4-methoxybenzylamine gave the corresponding isoglutamine, which then provided the key CBZ-protected N-PMB-glutarimide 14 after dehydration. Deprotection of both the CBZ and PMB groups followed by phthalimidation and deacetylation of the 3-amino-5-acetoxyglutarimide 16 afforded 2.

  DOI：

  10.1021/jo0514772

文献信息

• ORGANIC COMPOUNDS
  申请人：Givaudan SA

  公开号：EP2770849A1

  公开（公告）日：2014-09-03
• US20140272065A1
  申请人：——

  公开号：US20140272065A1

  公开（公告）日：2014-09-18
• [EN] ORGANIC COMPOUNDS<br/>[FR] COMPOSÉS ORGANIQUES
  申请人：GIVAUDAN SA

  公开号：WO2013060815A1

  公开（公告）日：2013-05-02

  4-substituted glutamic acid derivatives according to the formula (I) or their physiologically acceptable salts (I) wherein X is selected from CH3, phenyl, COOH and OH, are useful to impart, enhance or modify umami-and/or salt taste in a comestible product.