3(S)-isobutyl-5(R)-(2-methoxy-ethoxy)-4(S)-vinyl-tetrahydro-furan-2(S)-carboxylic acid, tert-butoxycarbonyl-trityloxy-amide | 310890-18-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 3(S)-isobutyl-5(R)-(2-methoxy-ethoxy)-4(S)-vinyl-tetrahydro-furan-2(S)-carboxylic acid, tert-butoxycarbonyl-trityloxy-amide
• CAS: 310890-18-7
• 化学式: C₃₈H₄₇NO₇
• 分子量: 629.794
• InChiKey: NJRPZINNCOHUDD-UJWBSGRQSA-N

物化性质

• 沸点：
  690.1±65.0 °C(predicted)
• 密度：
  1.15±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.53
• 重原子数：
  46.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  83.53
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3(S)-isobutyl-5(R)-(2-methoxy-ethoxy)-4(S)-vinyl-tetrahydro-furan-2(S)-carboxylic acid, tert-butoxycarbonyl-trityloxy-amide 在 臭氧 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以70%的产率得到4(R)-formyl-3(S)-isobutyl-5(R)-(2-methoxy-ethoxy)-tetrahydro-furan-2(S)-carboxylic acid, tert-butoxycarbonyl-trityloxy-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 、 1-羟基苯并三唑 、 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 为溶剂， 反应 16.0h， 生成 3(S)-isobutyl-5(R)-(2-methoxy-ethoxy)-4(S)-vinyl-tetrahydro-furan-2(S)-carboxylic acid, tert-butoxycarbonyl-trityloxy-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