(S)-2-(4-{(S)-1-[4-((S)-5-Benzyloxycarbonylamino-1-tert-butoxycarbonylamino-pentyl)-[1,2,3]triazol-1-yl]-2-phenyl-ethyl}-[1,2,3]triazol-1-yl)-3-phenyl-propionic acid methyl ester | 872864-33-0

• 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: (S)-2-(4-{(S)-1-[4-((S)-5-Benzyloxycarbonylamino-1-tert-butoxycarbonylamino-pentyl)-[1,2,3]triazol-1-yl]-2-phenyl-ethyl}-[1,2,3]triazol-1-yl)-3-phenyl-propionic acid methyl ester
• 英文别名: methyl (2S)-2-[4-[(1S)-1-[4-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]-5-(phenylmethoxycarbonylamino)pentyl]triazol-1-yl]-2-phenylethyl]triazol-1-yl]-3-phenylpropanoate
• CAS: 872864-33-0
• 化学式: C₄₀H₄₈N₈O₆
• 分子量: 736.871
• InChiKey: WOZZTXMBEBQQOD-PUBVIUOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  54
• 可旋转键数：
  21
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  164
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (S)-2-(4-{(S)-1-[4-((S)-5-Benzyloxycarbonylamino-1-tert-butoxycarbonylamino-pentyl)-[1,2,3]triazol-1-yl]-2-phenyl-ethyl}-[1,2,3]triazol-1-yl)-3-phenyl-propionic acid methyl ester 在 triflic azide 、 copper(II) sulfate 、 sodium ascorbate 、 三乙胺 、 三氟乙酸 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 33.0h， 生成 (S)-2-{4-[(S)-1-(4-{(S)-5-Benzyloxycarbonylamino-1-[4-((S)-5-benzyloxycarbonylamino-1-tert-butoxycarbonylamino-pentyl)-[1,2,3]triazol-1-yl]-pentyl}-[1,2,3]triazol-1-yl)-2-phenyl-ethyl]-[1,2,3]triazol-1-yl}-3-phenyl-propionic acid methyl ester
  参考文献：
  名称：

  Nonpeptidic Foldamers from Amino Acids:  Synthesis and Characterization of 1,3-Substituted Triazole Oligomers

  摘要：

  Nonpeptidic foldamers capable of displaying protein-like functionality were prepared by swapping amide bonds with 1,2,3-triazole rings. The overall conformation of these triazole oligomers is largely dictated by dipole-dipole interactions between adjacent rings. Solution NMR studies suggest that a zigzag conformation, which closely mimics the beta-strand structure, predominates in two different tetramers.

  DOI：

  10.1021/ja056406z
• 作为产物：
  描述：

  benzyl {(5S)-5-[(tert-butoxycarbonyl)amino]-6-oxohexyl}carbamate 在 正丁基锂 、 copper(II) sulfate 、 sodium ascorbate 、 三苯基膦 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 (S)-2-(4-{(S)-1-[4-((S)-5-Benzyloxycarbonylamino-1-tert-butoxycarbonylamino-pentyl)-[1,2,3]triazol-1-yl]-2-phenyl-ethyl}-[1,2,3]triazol-1-yl)-3-phenyl-propionic acid methyl ester
  参考文献：
  名称：

  Nonpeptidic Foldamers from Amino Acids:  Synthesis and Characterization of 1,3-Substituted Triazole Oligomers

  摘要：

  Nonpeptidic foldamers capable of displaying protein-like functionality were prepared by swapping amide bonds with 1,2,3-triazole rings. The overall conformation of these triazole oligomers is largely dictated by dipole-dipole interactions between adjacent rings. Solution NMR studies suggest that a zigzag conformation, which closely mimics the beta-strand structure, predominates in two different tetramers.

  DOI：

  10.1021/ja056406z

文献信息

• Solution- and Solid-Phase Synthesis of Triazole Oligomers That Display Protein-Like Functionality
  作者：Nicholas G. Angelo、Paramjit S. Arora

  DOI：10.1021/jo701292h

  日期：2007.10.1

  We recently developed a new class of oligomers that contain α-amino acid residues linked by 1,2,3-triazole groups [Angelo, N. G.; Arora, P. S. J. Am. Chem. Soc.2005,127, 17134−17135]. Synthesis of these oligomers involves an iterative sequence consisting of diazotransfer and Huisgen 1,3-dipolar cycloaddition steps. In this contribution, we describe an efficient one-pot, two-step sequence for the preparation

  我们最近开发了一种新型的低聚物，其包含通过1,2,3-三唑基连接的α-氨基酸残基[Angelo，NG; 阿罗拉，PS J. Am。化学 Soc。2005年，127，17134-17135]。这些低聚物的合成涉及由重氮转移和Huisgen 1,3-偶极环加成步骤组成的迭代序列。在这一贡献中，我们描述了一种有效的一锅两步程序，用于从溶液中相应的氨基酸衍生的胺和炔烃制备三唑。一锅法序列以比我们原始方法高得多的产率提供所需产物。我们还概述了在固相上合成这些基于三唑的仿生低聚物的高效方案。我们发现氨基酸衍生物和三唑环的迭代形成需要非传统的反应条件才能获得高收率。
• Methods for preparing nonpeptidic oligomers from amino acids
  申请人：Arora S. Paramjit

  公开号：US20070105917A1

  公开（公告）日：2007-05-10

  The present invention relates to nonpeptidic oligomers. Methods for preparing nonpeptidic oligomers from amino acids by replacing the amide bond with heterocyclic rings are also disclosed.

  本发明涉及非肽寡聚体。还公开了一种从氨基酸制备非肽寡聚体的方法，该方法通过用杂环环替换酰胺键来实现。
• Nonpeptidic Foldamers from Amino Acids:  Synthesis and Characterization of 1,3-Substituted Triazole Oligomers
  作者：Nicholas G. Angelo、Paramjit S. Arora

  DOI：10.1021/ja056406z

  日期：2005.12.1

  Nonpeptidic foldamers capable of displaying protein-like functionality were prepared by swapping amide bonds with 1,2,3-triazole rings. The overall conformation of these triazole oligomers is largely dictated by dipole-dipole interactions between adjacent rings. Solution NMR studies suggest that a zigzag conformation, which closely mimics the beta-strand structure, predominates in two different tetramers.