di-tert-butyl (2S,3S)-N-[6,7-bis(tert-butoxycarbonylmethoxy)coumarin-4-yl-methoxy]carbonyl-3-{3-[4-(trifluoromethyl)benzoyl]aminobenzyloxy}aspartate | 737830-22-7

• 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: di-tert-butyl (2S,3S)-N-[6,7-bis(tert-butoxycarbonylmethoxy)coumarin-4-yl-methoxy]carbonyl-3-{3-[4-(trifluoromethyl)benzoyl]aminobenzyloxy}aspartate
• CAS: 737830-22-7
• 化学式: C₅₀H₅₉F₃N₂O₁₆
• 分子量: 1001.02
• InChiKey: HEZGNJMFTZTUFR-YATWDLPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.37
• 重原子数：
  71.0
• 可旋转键数：
  17.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  230.53
• 氢给体数：
  2.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  di-tert-butyl (2S,3S)-N-[6,7-bis(tert-butoxycarbonylmethoxy)coumarin-4-yl-methoxy]carbonyl-3-{3-[4-(trifluoromethyl)benzoyl]aminobenzyloxy}aspartate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以49%的产率得到(2S,3S)-2-(6,7-Bis-carboxymethoxy-2-oxo-2H-chromen-4-ylmethoxycarbonylamino)-3-[3-(4-trifluoromethyl-benzoylamino)-benzyloxy]-succinic acid
  参考文献：
  名称：

  Synthesis of carbamate-type caged derivatives of a novel glutamate transporter blocker

  摘要：

  L-threa-beta-Benzyloxyaspartate (L-TBOA) and (2S,3S)-3-{3-[4-(trifluoromethyl)benzoylamino]benzyloxy}aspartate (L-TFB-TBOA) are potent nontransportable blockers for glutamate transporters. We synthesized a carbamate-type coumarin derivative of L-TBOA 3a as a caged blocker and compared 3a with the corresponding ester-type analogs 1. The carbamate 3a was less sensitive to photolysis than the ester I but was more stable in the aqueous solution. The [6,7-bis(carboxymethoxy)-coumarin-4yl]methylcarbonyl (BCMCMC) group exhibited good results both in photoreactivity and stability. Therefore, we examined photolysis of N-BCMCMC-TBOA 3b and N-BCMCMC-TFB-TBOA 4, which immediately released blockers to show glutamate uptake inhibition. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.011
• 作为产物：
  描述：

  6,7-bis(tert-butoxycarbonylmethoxy)-4-(hydroxymethoxy)coumarin 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.17h， 生成 di-tert-butyl (2S,3S)-N-[6,7-bis(tert-butoxycarbonylmethoxy)coumarin-4-yl-methoxy]carbonyl-3-{3-[4-(trifluoromethyl)benzoyl]aminobenzyloxy}aspartate
  参考文献：
  名称：

  Synthesis of carbamate-type caged derivatives of a novel glutamate transporter blocker

  摘要：

  L-threa-beta-Benzyloxyaspartate (L-TBOA) and (2S,3S)-3-{3-[4-(trifluoromethyl)benzoylamino]benzyloxy}aspartate (L-TFB-TBOA) are potent nontransportable blockers for glutamate transporters. We synthesized a carbamate-type coumarin derivative of L-TBOA 3a as a caged blocker and compared 3a with the corresponding ester-type analogs 1. The carbamate 3a was less sensitive to photolysis than the ester I but was more stable in the aqueous solution. The [6,7-bis(carboxymethoxy)-coumarin-4yl]methylcarbonyl (BCMCMC) group exhibited good results both in photoreactivity and stability. Therefore, we examined photolysis of N-BCMCMC-TBOA 3b and N-BCMCMC-TFB-TBOA 4, which immediately released blockers to show glutamate uptake inhibition. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.011