2(S)-acetylamino-N-[5(S)-hydroxymethyl-4(S)-isobutyl-2(R)-(2-methoxy-ethoxy)-tetrahydro-furan-3(S)-yl]-3-phenyl-propionamide | 310890-56-3

• 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: 2(S)-acetylamino-N-[5(S)-hydroxymethyl-4(S)-isobutyl-2(R)-(2-methoxy-ethoxy)-tetrahydro-furan-3(S)-yl]-3-phenyl-propionamide
• CAS: 310890-56-3
• 化学式: C₂₃H₃₆N₂O₆
• 分子量: 436.549
• InChiKey: NBTLUFOGXRMSMX-HVJVJISESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.26
• 重原子数：
  31.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  106.12
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2(S)-acetylamino-N-[5(S)-hydroxymethyl-4(S)-isobutyl-2(R)-(2-methoxy-ethoxy)-tetrahydro-furan-3(S)-yl]-3-phenyl-propionamide 在 N-甲基吗啉 、 sodium chlorite 、 sodium dihydrogenphosphate 、 四丙基高钌酸铵 、 2-甲基-2-丁烯 、 4 A molecular sieve 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 3.0h， 生成 4(S)-(2(S)-acetylamino-3-phenyl-propionylamino)-3(S)-isobutyl-5(R)-(2-methoxy-ethoxy)-tetrahydro-furan-2(S)-carboxylic acid
  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：

  5(S)-(tert-butyl-diphenyl-silanyloxymethyl)-4(S)-isobutyl-2(R)-(2-methoxy-ethoxy)-tetrahydro-furan-3(S)-ylamine 在 N-甲基吗啉 、 四丁基氟化铵 、 1-羟基苯并三唑 、 溶剂黄146 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 2(S)-acetylamino-N-[5(S)-hydroxymethyl-4(S)-isobutyl-2(R)-(2-methoxy-ethoxy)-tetrahydro-furan-3(S)-yl]-3-phenyl-propionamide
  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