N-benzyloxycarbonyl-γ-hydroxyglutamic acid lactone | 92030-03-0

• 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: N-benzyloxycarbonyl-γ-hydroxyglutamic acid lactone
• 英文别名: N-Benzyloxycarbonyl-DL-γ-hydroxy-glutaminsaeure-lacton；5-Oxo-4-(phenylmethoxycarbonylamino)oxolane-2-carboxylic acid
• CAS: 92030-03-0
• 化学式: C₁₃H₁₃NO₆
• 分子量: 279.249
• InChiKey: OWVIPWGMVXUJQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-γ-hydroxyglutamic acid lactone 、 4-甲氧基苄胺 以 吡啶 为溶剂， 反应 16.0h， 以85%的产率得到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：

  hydroxyglutamic acid 在 盐酸 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 48.0h， 生成 N-benzyloxycarbonyl-γ-hydroxyglutamic acid lactone
  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

• Synthesis of Racemic <i>cis</i>-5-Hydroxy-3-phthalimidoglutarimide. A Metabolite of Thalidomide Isolated from Human Plasma
  作者：Frederick A. Luzzio、Damien Y. Duveau、Erin R. Lepper、William D. Figg

  DOI：10.1021/jo0514772

  日期：2005.11.1

  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.