(S)-N-((S)-1-amino-3-methyl-1-oxobutan-2-yl)-1-((3R,4R)-1-benzyl-4-tosylamidopiperidin-3-yl)pyrrolidine-2-carboxamide | 1579997-52-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (S)-N-((S)-1-amino-3-methyl-1-oxobutan-2-yl)-1-((3R,4R)-1-benzyl-4-tosylamidopiperidin-3-yl)pyrrolidine-2-carboxamide
• CAS: 1579997-52-6
• 化学式: C₂₉H₄₁N₅O₄S
• 分子量: 555.742
• InChiKey: FOIDILBCXIFSNQ-RAVGUYNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  39.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  124.84
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-N-((S)-1-amino-3-methyl-1-oxobutan-2-yl)-1-((3R,4R)-1-benzyl-4-tosylamidopiperidin-3-yl)pyrrolidine-2-carboxamide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲苯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 30.0h， 以76%的产率得到(S)-N-((S)-1-amino-3-methyl-1-oxobutan-2-yl)-((3R,4R)-4-tosylamidopiperidin-3-yl)pyrrolidine-2-carboxamide
  参考文献：
  名称：

  Asymmetric Modular Synthesis of a Semirigid Dipeptide Mimetic by Cascade Cycloaddition/Ring Rearrangement and Borohydride Reduction

  摘要：

  A new semirigid dipeptide mimetic was prepared on multigram scale, in good yield, and in a stereocontrolled way, starting from commercially available and unexpensive reagents, i.e., N-benzylpiperidone, tosyl azide, and proline methyl ester. The optimized multicomponent process consisted of a cascade click cycloaddition and a ring rearrangement reaction, followed by a reductive step. Theoretical calculations were performed to elucidate the reaction mechanism and support the stereochemical outcome of the reduction. Finally, the new scaffold was used for the preparation of model peptidomimetics, whose beta turn conformation was confirmed by dynamic NMR experiments.

  DOI：

  10.1021/jo500237j
• 作为产物：
  描述：

  对甲苯磺酰叠氮 在 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.75h， 生成 (S)-N-((S)-1-amino-3-methyl-1-oxobutan-2-yl)-1-((3R,4R)-1-benzyl-4-tosylamidopiperidin-3-yl)pyrrolidine-2-carboxamide
  参考文献：
  名称：

  Asymmetric Modular Synthesis of a Semirigid Dipeptide Mimetic by Cascade Cycloaddition/Ring Rearrangement and Borohydride Reduction

  摘要：

  A new semirigid dipeptide mimetic was prepared on multigram scale, in good yield, and in a stereocontrolled way, starting from commercially available and unexpensive reagents, i.e., N-benzylpiperidone, tosyl azide, and proline methyl ester. The optimized multicomponent process consisted of a cascade click cycloaddition and a ring rearrangement reaction, followed by a reductive step. Theoretical calculations were performed to elucidate the reaction mechanism and support the stereochemical outcome of the reduction. Finally, the new scaffold was used for the preparation of model peptidomimetics, whose beta turn conformation was confirmed by dynamic NMR experiments.

  DOI：

  10.1021/jo500237j