1-O-benzyl 2-O-tert-butyl 4-O-(triazolo[4,5-b]pyridin-3-yl) (2S,4S)-4-(benzylamino)pyrrolidine-1,2,4-tricarboxylate | 1205681-56-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-O-benzyl 2-O-tert-butyl 4-O-(triazolo[4,5-b]pyridin-3-yl) (2S,4S)-4-(benzylamino)pyrrolidine-1,2,4-tricarboxylate
• CAS: 1205681-56-6
• 化学式: C₃₀H₃₂N₆O₆
• 分子量: 572.621
• InChiKey: AMGSASHQSPAWPM-NGQVCNFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  42
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-O-benzyl 2-O-tert-butyl 4-O-(triazolo[4,5-b]pyridin-3-yl) (2S,4S)-4-(benzylamino)pyrrolidine-1,2,4-tricarboxylate 在 氢溴酸 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.5h， 生成 (3S,5S)-6-benzyl-8,8-dimethyl-9-(naphthalen-1-ylmethyl)-7,10-dioxo-2,6,9-triazaspiro[4,5]decane-3-carboxylic acid trifluoroacetic acid
  参考文献：
  名称：

  Hydrophobic Substituent Effects on Proline Catalysis of Aldol Reactions in Water

  摘要：

  Derivatives of 4-hydroxyproline with a series of hydrophobic groups in well-defined orientations have been tested as catalysts for the aldol reactions. All of the modified proline catalysts carry out the intermolecular aldol reaction in water and provide high diastereoselectivity and enantioselectivity. Modified prolines with aromatic groups syn to the carboxylic acid are better catalysts than those with small hydrophobic groups (1a is 43.5 times faster than 1f). Quantum mechanical calculations provide transition structures, TS-1a(water) and TS-1f(water), that support the hypothesis that a stabilizing hydrophobic interaction occurs with 1a.

  DOI：

  10.1021/jo300569c
• 作为产物：
  描述：

  (3S,5S)-3-amino-1-((benzyloxy)carbonyl)-5-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid 在 sodium cyanoborohydride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.67h， 生成 1-O-benzyl 2-O-tert-butyl 4-O-(triazolo[4,5-b]pyridin-3-yl) (2S,4S)-4-(benzylamino)pyrrolidine-1,2,4-tricarboxylate
  参考文献：
  名称：

  Hydrophobic Substituent Effects on Proline Catalysis of Aldol Reactions in Water

  摘要：

  Derivatives of 4-hydroxyproline with a series of hydrophobic groups in well-defined orientations have been tested as catalysts for the aldol reactions. All of the modified proline catalysts carry out the intermolecular aldol reaction in water and provide high diastereoselectivity and enantioselectivity. Modified prolines with aromatic groups syn to the carboxylic acid are better catalysts than those with small hydrophobic groups (1a is 43.5 times faster than 1f). Quantum mechanical calculations provide transition structures, TS-1a(water) and TS-1f(water), that support the hypothesis that a stabilizing hydrophobic interaction occurs with 1a.

  DOI：

  10.1021/jo300569c

文献信息

• [EN] SYNTHESIS OF BIS-PEPTIDES OLIGOMERS COMPRISING AT LEAST ONE N-SUBSTITUTED DIKETOPIPERAZINE AS STRUCTURAL MOIETY<br/>[FR] SYNTHÈSE D'OLIGOMÈRES DE BIS-PEPTIDES COMPORTANT AU MOINS UNE DICÉTOPIPÉRAZINE N-SUBSTITUÉE EN TANT QUE GROUPE FONCTIONNEL STRUCTUREL
  申请人：UNIV TEMPLE

  公开号：WO2010009196A1

  公开（公告）日：2010-01-21

  Functionalized bis-peptides as well as other amide-containing compounds are obtained by acylation of hindered amines. The functionalized bis-peptides are useful as shape-programmable nanostructures that are immune to denaturation and that contain arrays of functional groups having designed catalytic, protein-binding and/or sensor capabilities.

  通过酰化难处理胺，获得了功能化的双肽以及其他含酰胺化合物。这些功能化的双肽可用作形状可编程的纳米结构，不易变性，并含有设计的催化、蛋白结合和/或传感器功能的功能团阵列。
• Synthesis of Hexa- and Pentasubstituted Diketopiperazines from Sterically Hindered Amino Acids
  作者：Zachary Z. Brown、Christian E. Schafmeister

  DOI：10.1021/ol100048g

  日期：2010.4.2

  Steric hindrance assists in the formation of hindered diketopiperazines using acyl-transfer coupling. In acyl-transfer coupling, the carboxylate of an unprotected N-alkylamino acid attacks an active ester to form a transient anhydride that undergoes an O,N acyl transfer to form a tertiary amide. If the active ester is part of an N-alkylamino acid it will form a diketopiperazine. It is demonstrated here that acyl-transfer coupling can assemble highly functionalized bis-peptides bearing a functional group on every monomer.
• Hydrophobic Substituent Effects on Proline Catalysis of Aldol Reactions in Water
  作者：Qingquan Zhao、Yu-hong Lam、Mahboubeh Kheirabadi、Chongsong Xu、K. N. Houk、Christian E. Schafmeister

  DOI：10.1021/jo300569c

  日期：2012.5.18

  Derivatives of 4-hydroxyproline with a series of hydrophobic groups in well-defined orientations have been tested as catalysts for the aldol reactions. All of the modified proline catalysts carry out the intermolecular aldol reaction in water and provide high diastereoselectivity and enantioselectivity. Modified prolines with aromatic groups syn to the carboxylic acid are better catalysts than those with small hydrophobic groups (1a is 43.5 times faster than 1f). Quantum mechanical calculations provide transition structures, TS-1a(water) and TS-1f(water), that support the hypothesis that a stabilizing hydrophobic interaction occurs with 1a.