(E)-dibenzyl 2-benzylfumarate | 1365265-51-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-dibenzyl 2-benzylfumarate
• 英文别名: dibenzyl (E)-2-benzylbut-2-enedioate
• CAS: 1365265-51-5
• 化学式: C₂₅H₂₂O₄
• 分子量: 386.447
• InChiKey: YZDWJOKYDZJUCP-HAVVHWLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-dibenzyl 2-benzylfumarate 在 potassium osmate(VI) dihydrate 、 水 、 chloroamine-T 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 作用下， 以 乙腈 为溶剂， 反应 1.5h， 生成 dibenzyl (2S,3S)-2-benzyl-2,3-dihydroxysuccinate
  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
• 作为产物：
  描述：

  dibenzyl L-malate 在 六甲基磷酰三胺 、 邻苯二甲酸亚胺 、 偶氮二甲酸二异丙酯 、 三苯基膦 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 dibenzyl 2-benzylidenesuccinate 、 (E)-dibenzyl 2-benzylfumarate
  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.