N¹-tert-butoxycarbonyl-1-(benzylthiomethyl)ethylenediamine | 1069127-52-1

• 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: N¹-tert-butoxycarbonyl-1-(benzylthiomethyl)ethylenediamine
• 英文别名: tert-butyl N-[(2R)-1-amino-3-benzylsulfanylpropan-2-yl]carbamate
• CAS: 1069127-52-1
• 化学式: C₁₅H₂₄N₂O₂S
• 分子量: 296.434
• InChiKey: PQSYPFRIEGNURH-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  89.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲酸 、 N¹-tert-butoxycarbonyl-1-(benzylthiomethyl)ethylenediamine 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以87%的产率得到Boc-Cys(Bzl)-ψ[CH2NHCHO]
  参考文献：
  名称：

  Isoselenocyanates derived from Boc/Z-amino acids: synthesis, isolation, characterization, and application to the efficient synthesis of unsymmetrical selenoureas and selenoureidopeptidomimetics

  摘要：

  Isoselenocyanates derived from Boc/Z-amino acids are prepared by the reaction of the corresponding isonitriles with selenium powder in presence of triethylamine at reflux. The utility of these new classes of isoselenocyanates in the preparation of selenoureidodipeptidomimetics possessing both amino as well as carboxy termini has been accomplished. The H-1 NMR analysis confirmed that the protocol involving the conversion of isonitriles to isoselenocyanates and their use as coupling agents in assembling selenour-eido derivatives is free from racemization. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.082
• 作为产物：
  描述：

  N-tert-butoxycarbonyl-2-azido-1-(benzylthiomethyl)ethylamine 在 palladium on activated charcoal 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 N¹-tert-butoxycarbonyl-1-(benzylthiomethyl)ethylenediamine
  参考文献：
  名称：

  γ-巯基甲基 PNA 单体的新合成路线

  摘要：

  摘要 肽核酸 (PNA) 是一种寡核苷酸模拟物，广泛用作反义、反基因分子和生物技术工具。最近，已经开发了几种基于 PNA 的微阵列和其他生物传感器。用于 DNA 检测的 PNA 分子信标或发光探针的构建需要对 PNA 部分进行标记。标签通常通过柔性接头连接在 C 或 N 末端，或连接在 PNA 序列的中间，用人工碱基替换一个 PNA 碱基或通过将荧光团连接到修饰的 PNA 骨架。开发简单的协议来标记 PNA 的需要鼓励我们设计一种新的程序来合成 γ-巯基甲基修饰的 PNA。在这里，我们提出了一种合成带有氨基酸侧链的修饰 PNA 的新策略。

  DOI：

  10.1080/00397910802219122

文献信息

• <i>N</i>-Urethane-Protected Amino Alkyl Isothiocyanates: Synthesis, Isolation, Characterization, and Application to the Synthesis of Thioureidopeptides
  作者：Vommina V. Sureshbabu、Shankar A. Naik、H. P. Hemantha、N. Narendra、Ushati Das、Tayur N. Guru Row

  DOI：10.1021/jo900675s

  日期：2009.8.7

  Synthetically useful N-Fmoc amino-alkyl isothiocyanates have been described, starting from protected amino acids. These compounds have been synthesized in excellent yields by thiocarbonylation of the monoprotected 1,2-diamines with CS2/TEA/p-TsCl, isolated as stable solids, and completely characterized. The procedure has been extended to the synthesis of amino alkyl isothiocyanates from Boc- and Z-protected amino acids as well. The utility of these isothiocyanates for peptidomimetics synthesis has been demonstrated by employing them in the preparation of a series of dithioureidopeptide esters. Boc-Gly-OH and Boc-Phe-OH derived isothiocyanates 9a and 9c have been obtained as single crystals and their structures solved through X-ray diffraction. They belong to the orthorhombic crystal system, and have a single molecule in the asymmetric unit (Z' = 1). 9a crystallizes in the centrosymmetric space group Pbca, while 9c crystallizes in the noncentrosymmetric space group P2(1)2(1)2(1).
• Isoselenocyanates derived from Boc/Z-amino acids: synthesis, isolation, characterization, and application to the efficient synthesis of unsymmetrical selenoureas and selenoureidopeptidomimetics
  作者：Gundala Chennakrishnareddy、Govindappa Nagendra、Hosahalli P. Hemantha、Ushati Das、Tayur N. Guru Row、Vommina V. Sureshbabu

  DOI：10.1016/j.tet.2010.06.082

  日期：2010.8

  Isoselenocyanates derived from Boc/Z-amino acids are prepared by the reaction of the corresponding isonitriles with selenium powder in presence of triethylamine at reflux. The utility of these new classes of isoselenocyanates in the preparation of selenoureidodipeptidomimetics possessing both amino as well as carboxy termini has been accomplished. The H-1 NMR analysis confirmed that the protocol involving the conversion of isonitriles to isoselenocyanates and their use as coupling agents in assembling selenour-eido derivatives is free from racemization. (C) 2010 Elsevier Ltd. All rights reserved.
• New Synthetic Route to <font>γ</font>-Mercaptomethyl PNA Monomers
  作者：Soccorsa Pensato、Luca Domenico D'Andrea、Carlo Pedone、Alessandra Romanelli

  DOI：10.1080/00397910802219122

  日期：2008.7.24

  with an artificial base or by attaching fluorophores to a modified PNA backbone. The need to develop simple protocols to label PNAs encouraged us to design a new procedure for the synthesis of γ-mercaptomethyl-modified PNA. Here we propose a new strategy for the synthesis of modified PNAs, bearing amino acid side chains. The synthesis is straightforward and is an improvement to the procedures reported

  摘要 肽核酸 (PNA) 是一种寡核苷酸模拟物，广泛用作反义、反基因分子和生物技术工具。最近，已经开发了几种基于 PNA 的微阵列和其他生物传感器。用于 DNA 检测的 PNA 分子信标或发光探针的构建需要对 PNA 部分进行标记。标签通常通过柔性接头连接在 C 或 N 末端，或连接在 PNA 序列的中间，用人工碱基替换一个 PNA 碱基或通过将荧光团连接到修饰的 PNA 骨架。开发简单的协议来标记 PNA 的需要鼓励我们设计一种新的程序来合成 γ-巯基甲基修饰的 PNA。在这里，我们提出了一种合成带有氨基酸侧链的修饰 PNA 的新策略。