benzyl N-[(5S)-5-[(2-methylpropan-2-yl)oxycarbonylamino]hept-6-ynyl]carbamate | 143327-80-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl N-[(5S)-5-[(2-methylpropan-2-yl)oxycarbonylamino]hept-6-ynyl]carbamate
• CAS: 143327-80-4
• 化学式: C₂₀H₂₈N₂O₄
• 分子量: 360.453
• InChiKey: VANORBGYPGEOCF-QGZVFWFLSA-N

物化性质

• 沸点：
  522.4±50.0 °C(Predicted)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl N-[(5S)-5-[(2-methylpropan-2-yl)oxycarbonylamino]hept-6-ynyl]carbamate 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 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 81.0h， 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 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 benzyl N-[(5S)-5-[(2-methylpropan-2-yl)oxycarbonylamino]hept-6-ynyl]carbamate
  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

• Backbone-Fluorinated 1,2,3-Triazole-Containing Dipeptide Surrogates
  作者：Jens Engel-Andreasen、Isabelle Wellhöfer、Kathrine Wich、Christian A. Olsen

  DOI：10.1021/acs.joc.7b01744

  日期：2017.11.3

  incorporated as a peptide bond bioisostere to provide protease resistance in peptidomimetics. Herein, we report the synthesis of peptidomimetic building blocks containing backbone-fluorinated 1,4-disubstituted 1,2,3-triazole moieties. Synthetic protocols for the preparation of various Xaa-Gly dipeptide surrogates in the form of Xaa-ψ[triazole]-F2Gly building blocks were established, and selected examples were

  可以将1,2,3-三唑部分作为肽键生物等排体掺入以在拟肽中提供蛋白酶抗性。在这里，我们报道了含有骨架氟化的1，4-二取代的1,2,3-三唑部分的拟肽结构单元的合成。建立了用于制备Xaa-ψ[triazole] -F 2 Gly结构单元形式的各种Xaa-Gly二肽替代物的合成方案，并将选定的实例引入作为模型化合物的内源性阿片受体阿片受体配体亮脑啡肽。
• Preparation and reactions of chiral propargylic amines
  作者：James R. Hauske、Peter Dorff、Susan Julin、Gary Martinelli、Jacqueline Bussolari

  DOI：10.1016/0040-4039(92)80006-6

  日期：1992.6

  Exposure of chiral amino aldehydes (1) to dimethyl diazophosphonate (4) affords propargylic amines (2) of high optical purity. Chain extension of these intermediates is readily accomplished via hydrozirconation of the acetylene moiety and subsequent Ni(II) catalyzed Michael addition to a variety of Michael acceptors.

  将手性氨基醛（1）暴露于重氮膦酸二甲酯（4）可获得高光学纯度的炔丙基胺（2）。这些中间体的扩链很容易通过乙炔部分的加氢锆化和随后的Ni（II）催化的Michael加成到各种Michael受体上而实现。
• 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。
• A reasonably stereospecific multistep conversion of Boc-protected α-amino acids to Phth-protected β3-amino acids
  作者：Andrea Temperini、Antonella Capperucci、Alessandro Degl’Innocenti、Raffaella Terlizzi、Marcello Tiecco

  DOI：10.1016/j.tetlet.2010.05.143

  日期：2010.8

  A method for the synthesis of beta(3)-amino acids starting from alpha-amino acids is described. This conversion can be effected by an eight-step procedure which involves the transformation of the carboxylic group into an alkyne followed by a selenium-mediated conversion of the carbon-carbon triple bond to a Se-phenyl selenocarboxylate intermediate. The reactive Se-phenyl selenocarboxylate intermediates can be trapped with water, alcohols or the amine of an amino acid derivative to give beta(3)-amino acids, beta(3)-amino esters or mixed peptides, respectively. The whole transformations of the carboxylic group into an alkyne and of the alkyne group into beta(3)-amino acids may not require purification of the intermediate products but a workup and isolation procedure of crude materials. (C) 2010 Elsevier Ltd. All rights reserved.