3(S)-isobutyl-5(S)-(2-methoxy-ethoxy)-tetrahydro-furan-2(S),4(R)-dicarboxylic acid 2-(tert-butoxycarbonyl-trityloxy-amide) 4-[(1-methylcarbamoyl-2(R)-phenyl-ethyl)amide] | 310890-30-3

• 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: 3(S)-isobutyl-5(S)-(2-methoxy-ethoxy)-tetrahydro-furan-2(S),4(R)-dicarboxylic acid 2-(tert-butoxycarbonyl-trityloxy-amide) 4-[(1-methylcarbamoyl-2(R)-phenyl-ethyl)amide]
• CAS: 310890-30-3
• 化学式: C₄₇H₅₇N₃O₉
• 分子量: 807.984
• InChiKey: LXGOLOZRRHVCIO-WCLLRKIYSA-N

物化性质

• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.81
• 重原子数：
  59.0
• 可旋转键数：
  17.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  141.73
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3(S)-isobutyl-5(S)-(2-methoxy-ethoxy)-tetrahydro-furan-2(S),4(R)-dicarboxylic acid 2-(tert-butoxycarbonyl-trityloxy-amide) 4-[(1-methylcarbamoyl-2(R)-phenyl-ethyl)amide] 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以57%的产率得到3(S)-isobutyl-5(R)-(2-methoxy-ethoxy)-tetrahydro-furan-2(S),4(S)-dicarboxylic acid 2-hydroxyamide 4-[(1-methylcarbamoyl-2(R)-phenyl-ethyl)amide]
  参考文献：
  名称：

  Tetrahydrofuran as a Scaffold for Peptidomimetics. Application to the Design and Synthesis of Conformationally Constrained Metalloproteinase Inhibitors

  摘要：

  Enantiopure functionalized tetrahydrofurans were synthesized as prototypical conformationally constrained analogs of acyclic succinic acid-based inhibitors of metalloproteinases. While preliminary docking study showed good congruence with a potent inhibitor, the biological results were disappointing. Molecular dynamics simulation revealed the weakness of the H-bond interactions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00687-6
• 作为产物：
  描述：

  3(S)-isobutyl-5(R)-(2-methoxy-ethoxy)-4(S)-vinyl-tetrahydro-furan-2(S)-carboxylic acid 在 N-甲基吗啉 、 4-二甲氨基吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 1-羟基苯并三唑 、 臭氧 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 34.25h， 生成 3(S)-isobutyl-5(S)-(2-methoxy-ethoxy)-tetrahydro-furan-2(S),4(R)-dicarboxylic acid 2-(tert-butoxycarbonyl-trityloxy-amide) 4-[(1-methylcarbamoyl-2(R)-phenyl-ethyl)amide]
  参考文献：
  名称：

  Tetrahydrofuran as a Scaffold for Peptidomimetics. Application to the Design and Synthesis of Conformationally Constrained Metalloproteinase Inhibitors

  摘要：

  Enantiopure functionalized tetrahydrofurans were synthesized as prototypical conformationally constrained analogs of acyclic succinic acid-based inhibitors of metalloproteinases. While preliminary docking study showed good congruence with a potent inhibitor, the biological results were disappointing. Molecular dynamics simulation revealed the weakness of the H-bond interactions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00687-6