(2S,3S)-3-amino-2-benzyl-2-hydroxysuccinic acid | 1365265-61-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2S,3S)-3-amino-2-benzyl-2-hydroxysuccinic acid
• 英文别名: (2S,3S)-3-amino-2-benzyl-2-hydroxybutanedioic acid
• CAS: 1365265-61-7
• 化学式: C₁₁H₁₃NO₅
• 分子量: 239.228
• InChiKey: WKMISARKAWMWQX-KCJUWKMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  121
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (E)-dibenzyl 2-benzylfumarate 在 potassium osmate(VI) dihydrate 、 水 、 氢溴酸 、 溶剂黄146 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 lithium hydroxide 、 苯酚 作用下， 以 水 、 乙腈 为溶剂， 反应 71.83h， 生成 (2S,3S)-3-amino-2-benzyl-2-hydroxysuccinic acid
  参考文献：
  名称：

  A focus on the asymmetric synthesis of a novel threo-β-benzyl-β-hydroxy aspartate analogue

  摘要：

  Considering the biological activity of beta-alkyl-beta-hydroxyaspartate derivatives as potent blockers of glutamate transporters (EAATs) impacting on glutamatergic synapses activity, we have developed a concise, asymmetric synthesis of enantiomerically pure threo-beta-benzyl-beta-hydroxyaspartates. The key step is a regiospecific and stereoselective Sharpless asymmetric aminohydroxylation (SAA) on previously synthesized benzyl fumarate. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.01.004

文献信息

• A focus on the asymmetric synthesis of a novel threo-β-benzyl-β-hydroxy aspartate analogue
  作者：Sofiane Mekki、Salima Bellahouel、Nicolas Vanthuyne、Marc Rolland、Aicha Derdour、Jean Martinez、Michel Vignes、Valérie Rolland

  DOI：10.1016/j.tetasy.2012.01.004

  日期：2012.1

  Considering the biological activity of beta-alkyl-beta-hydroxyaspartate derivatives as potent blockers of glutamate transporters (EAATs) impacting on glutamatergic synapses activity, we have developed a concise, asymmetric synthesis of enantiomerically pure threo-beta-benzyl-beta-hydroxyaspartates. The key step is a regiospecific and stereoselective Sharpless asymmetric aminohydroxylation (SAA) on previously synthesized benzyl fumarate. (C) 2012 Elsevier Ltd. All rights reserved.