[4(S)-azido-3(S)-isobutyl-5(R)-(2-methoxy-ethoxy)-tetrahydro-furan-2(S)-ylmethoxy]-tert-butyl-diphenyl-silane | 310890-42-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: [4(S)-azido-3(S)-isobutyl-5(R)-(2-methoxy-ethoxy)-tetrahydro-furan-2(S)-ylmethoxy]-tert-butyl-diphenyl-silane
• CAS: 310890-42-7
• 化学式: C₂₈H₄₁N₃O₄Si
• 分子量: 511.737
• InChiKey: ZLMGWLJQZDYQSI-JVYGEBFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.29
• 重原子数：
  36.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  85.68
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [4(S)-azido-3(S)-isobutyl-5(R)-(2-methoxy-ethoxy)-tetrahydro-furan-2(S)-ylmethoxy]-tert-butyl-diphenyl-silane 在 palladium on activated charcoal 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 、 四丁基氟化铵 、 氢气 、 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 、 乙醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 38.0h， 生成 4(S)-(2(S)-acetylamino-3-phenyl-propionylamino)-3(S)-isobutyl-5(R)-(2-methoxy-ethoxy)-tetrahydro-furan-2(S)-carboxylic acid 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：

  Di-S-(2-pyridyl) dithiocarbonate 、 乙二醇甲醚 、 3(S)-azido-5(S)-(tert-butyl-diphenyl-silanyloxymethyl)-4(S)-isobutyl-tetrahydro-furan-2-ol 在 4 A molecular sieve 、 三乙胺 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 38.0h， 以53%的产率得到[4(S)-azido-3(S)-isobutyl-5(S)-(2-methoxy-ethoxy)-tetrahydro-furan-2(S)-ylmethoxy]-tert-butyl-diphenyl-silane
  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