5(S)-(tert-butyl-diphenyl-silanyloxymethyl)-4(S)-isobutyl-dihydro-furan-2-one | 310889-88-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 5(S)-(tert-butyl-diphenyl-silanyloxymethyl)-4(S)-isobutyl-dihydro-furan-2-one
• 英文别名: (4S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-(2-methylpropyl)oxolan-2-one
• CAS: 310889-88-4
• 化学式: C₂₅H₃₄O₃Si
• 分子量: 410.629
• InChiKey: VCXSDUPCCOQFLR-NZQKXSOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5(S)-(tert-butyl-diphenyl-silanyloxymethyl)-4(S)-isobutyl-dihydro-furan-2-one 在 palladium on activated charcoal 4 A molecular sieve 、 2,4,6-三异丙基苯磺酰叠氮化物 、 氢气 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 85.5h， 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
• 作为产物：
  描述：

  ISOBUTYLMAGNESIUM BROMIDE 、 (5S)-5-({[(2-甲基-2-丙基)(二苯基)硅烷基]氧基}甲基)-2(5H)-呋喃酮 在 copper(l) iodide 、 2,3-二巯基丁二酸 作用下， 以 四氢呋喃 为溶剂， 以98%的产率得到5(S)-(tert-butyl-diphenyl-silanyloxymethyl)-4(S)-isobutyl-dihydro-furan-2-one
  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