1-O-benzyl 2-O-tert-butyl 4-O-(triazolo[4,5-b]pyridin-3-yl) (2S,4S)-4-[3-(phenylmethoxycarbonylamino)propylamino]pyrrolidine-1,2,4-tricarboxylate | 1205681-64-6

• 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-[3-(phenylmethoxycarbonylamino)propylamino]pyrrolidine-1,2,4-tricarboxylate
• CAS: 1205681-64-6
• 化学式: C₃₄H₃₉N₇O₈
• 分子量: 673.726
• InChiKey: DDQYJHIICFVNHO-FOPBOCKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  49
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  176
• 氢给体数：
  2
• 氢受体数：
  12

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-[3-(phenylmethoxycarbonylamino)propylamino]pyrrolidine-1,2,4-tricarboxylate 、 在 N,N-二异丙基乙胺 、 N,N'-二异丙基碳二亚胺 、 氢溴酸 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 二氯甲烷 为溶剂， 反应 1.5h， 以59%的产率得到
  参考文献：
  名称：

  Synthesis of Hexa- and Pentasubstituted Diketopiperazines from Sterically Hindered Amino Acids

  摘要：

  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.

  DOI：

  10.1021/ol100048g
• 作为产物：
  描述：

  N-羟基-7-氮杂苯并三氮唑 、 (3S,5S)-1-((benzyloxy)carbonyl)-3-((3-(((benzyloxy)carbonyl)amino)propyl)amino)-5-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid 在 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 1-O-benzyl 2-O-tert-butyl 4-O-(triazolo[4,5-b]pyridin-3-yl) (2S,4S)-4-[3-(phenylmethoxycarbonylamino)propylamino]pyrrolidine-1,2,4-tricarboxylate
  参考文献：
  名称：

  Synthesis of Hexa- and Pentasubstituted Diketopiperazines from Sterically Hindered Amino Acids

  摘要：

  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.

  DOI：

  10.1021/ol100048g

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.