N-[5(S)-(tert-butyl-diphenyl-silanyloxymethyl)-4(S)-isobutyl-2(S)-(2-methoxy-ethoxy)-tetrahydro-furan-3(S)-yl]-4-methoxy-benzenesulfonamide | 310890-52-9

• 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: N-[5(S)-(tert-butyl-diphenyl-silanyloxymethyl)-4(S)-isobutyl-2(S)-(2-methoxy-ethoxy)-tetrahydro-furan-3(S)-yl]-4-methoxy-benzenesulfonamide
• CAS: 310890-52-9
• 化学式: C₃₅H₄₉NO₇SSi
• 分子量: 655.928
• InChiKey: ULUSPFGSCYUHLT-WZJLIZBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  45.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  92.32
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-[5(S)-(tert-butyl-diphenyl-silanyloxymethyl)-4(S)-isobutyl-2(S)-(2-methoxy-ethoxy)-tetrahydro-furan-3(S)-yl]-4-methoxy-benzenesulfonamide 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 、 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 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 3.0h， 生成 3(S)-isobutyl-4(S)-(4-methoxy-benzenesulfonylamino)-5(S)-(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：

  3(S)-azido-5(S)-(tert-butyl-diphenyl-silanyloxymethyl)-4(S)-isobutyl-tetrahydro-furan-2-ol 在 palladium on activated charcoal 4 A molecular sieve 、 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 74.0h， 生成 N-[5(S)-(tert-butyl-diphenyl-silanyloxymethyl)-4(S)-isobutyl-2(S)-(2-methoxy-ethoxy)-tetrahydro-furan-3(S)-yl]-4-methoxy-benzenesulfonamide
  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