2,2,2-trifluoro-N-(2-((2-(tritylamino)ethyl)amino)ethyl)-acetamide | 1373763-28-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2,2,2-trifluoro-N-(2-((2-(tritylamino)ethyl)amino)ethyl)-acetamide
• 英文别名: 2,2,2-trifluoro-N-[2-[2-(tritylamino)ethylamino]ethyl]acetamide
• CAS: 1373763-28-0
• 化学式: C₂₅H₂₆F₃N₃O
• 分子量: 441.496
• InChiKey: BHARSYIGUNILCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  53.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,2,2-trifluoro-N-(2-((2-(tritylamino)ethyl)amino)ethyl)-acetamide 在 水 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成
  参考文献：
  名称：

  Solid-Phase Synthesis of Asymmetrically Branched Sequence-Defined Poly/Oligo(amidoamines)

  摘要：

  We present for the first time the synthesis of asymmetrically branched sequence-defined poly/oligo(amidoamines) (PAAs) using solid-phase synthesis with the capability of introducing diversity at the side chains. We introduce two new versatile (diethylenetriamine) building blocks for solid-phase synthesis bearing Fmoc/Boc and Fmoc/Alloc protecting groups expanding recently used Fmoc/Boc protecting group strategy for linear PAAs to an Fmoc/Alloc/Boc strategy. This allows for orthogonal on-resin cleavage of Fmoc and Alloc protecting groups during solid-phase synthesis of PAAs with backbones differing in chain length and sequence. With these structures we then demonstrate the potential for generating asymmetrical branching by automated multiple on-resin cleavage of Alloc protecting groups as well as the introduction of side chains varying in length and number. Such systems have high potential as nonviral vectors for gene delivery and will allow for more detailed studies on the correlation between the degree of branching of PAAs and their resulting biological properties.

  DOI：

  10.1021/jo202561k
• 作为产物：
  描述：

  N-Ethyl-trifluoracetamid 、 N-(2-(triphenylmethyl)amino)ethyl-1,2-ethanediamine 以 四氢呋喃 为溶剂， 以90%的产率得到2,2,2-trifluoro-N-(2-((2-(tritylamino)ethyl)amino)ethyl)-acetamide
  参考文献：
  名称：

  Solid-Phase Synthesis of Asymmetrically Branched Sequence-Defined Poly/Oligo(amidoamines)

  摘要：

  We present for the first time the synthesis of asymmetrically branched sequence-defined poly/oligo(amidoamines) (PAAs) using solid-phase synthesis with the capability of introducing diversity at the side chains. We introduce two new versatile (diethylenetriamine) building blocks for solid-phase synthesis bearing Fmoc/Boc and Fmoc/Alloc protecting groups expanding recently used Fmoc/Boc protecting group strategy for linear PAAs to an Fmoc/Alloc/Boc strategy. This allows for orthogonal on-resin cleavage of Fmoc and Alloc protecting groups during solid-phase synthesis of PAAs with backbones differing in chain length and sequence. With these structures we then demonstrate the potential for generating asymmetrical branching by automated multiple on-resin cleavage of Alloc protecting groups as well as the introduction of side chains varying in length and number. Such systems have high potential as nonviral vectors for gene delivery and will allow for more detailed studies on the correlation between the degree of branching of PAAs and their resulting biological properties.

  DOI：

  10.1021/jo202561k

文献信息

• Synthesis of Carbohydrate-Functionalised Sequence-Defined Oligo(amidoamine)s by Photochemical ThiolEne Coupling in a Continuous Flow Reactor
  作者：Felix Wojcik、Alexander G. O'Brien、Sebastian Götze、Peter H. Seeberger、Laura Hartmann

  DOI：10.1002/chem.201203927

  日期：2013.2.25

  we report two complimentary strategies for the preparation of such sequence‐defined carbohydrate‐functionalised PAAs that use photochemical thiolene coupling (TEC) as an alternative to the established azide–alkyne cycloaddition (“click”) reaction. In the first approach, PAAs that contained multiple olefins were synthesised on a solid support from a new building block and subsequent conjugation with

  聚/低聚（酰胺基胺）（PAA）最近被公认为具有潜在的潜力，可以很好地定义多种碳水化合物的骨架，并可以作为多价配体。本文中，我们报告了使用光化学硫醇制备此类序列定义的碳水化合物官能化PAA的两种互补策略。烯偶联（TEC）作为已建立的叠氮化物-炔烃环加成（“喀哒”）反应的替代方法。在第一种方法中，在新载体的固体载体上合成包含多种烯烃的PAA，然后与未保护的硫代碳水化合物缀合。另外，可以使用TEC制备预功能化的构建基块，并将其组装在固体支持物上，以提供碳水化合物功能化的PAA。两种方法都依赖于连续流动光反应器用于TEC反应。由于其路径长度短，该系统是高效的，并且不需要额外的自由基引发剂。如O的反应所示，在Teflon AF-2400管中在254 nm处进行反应可为糖类偶联提供高效的TEC程序。烯丙基糖苷与硫醇。该方法允许在单个步骤中将PAA骨架上所有反应位点完全功能化，从而获得确定的均质序列。此外，在流动反应器中FEP管道中366
• Split-and-Combine Approach Towards Branched Precision Glycomacromolecules and Their Lectin Binding Behavior
  作者：Mischa Baier、Markus Giesler、Laura Hartmann

  DOI：10.1002/chem.201704179

  日期：2018.2.1

  the branching arm. In the second stage, the linear, glycosylated and alkynylated arms were then coupled to the end capped backbone via CuAAC. In this way, branched glycomacromolecules with two and three branches, respectively, have been synthesized carrying from two to six sugar residues per molecule. Both, linear arms and branched glycomacromolecules were then subjected to a lectin binding assay using

  以前，基于在固体支持物上分步组装的量身定制构建基块，可以实现糖配体的多价呈递，从而合成了单分散和序列控制的寡聚（酰胺基胺）支架。在这里，我们使用拆分结合方法扩展了这一概念，以访问线性和分支糖大分子小文库。叠氮化物侧链通过使用一种新型结构单元引入到支架中，该结构单元允许容易获得的炔丙基官能化聚糖的铜介导的叠氮化物-炔烃环加成（CuAAC）。在第一阶段中，将线性支架组装在固体支持物上之后，将批次分成两部分。树脂结合的低聚物的一部分被封端并进一步用作主链，另一部分被炔丙基化的α-官能团官能化。d-甘露吡喃糖苷在侧链中，末端被炔烃官能团封端，最后从固体支持物上裂解下来形成支链。在第二阶段中，然后将线性，糖基化和炔基化的臂通过CuAAC偶联至封端的骨架。以这种方式，已经合成了分别具有两个和三个分支的分支糖大分子，每个分子带有两个至六个糖残基。然后，使用表面等离振子共振（SPR）和模型凝集素伴刀豆球蛋白A（Con
• Heteromultivalent Glycooligomers as Mimetics of Blood Group Antigens
  作者：Katharina S. Bücher、Patrick B. Konietzny、Nicole L. Snyder、Laura Hartmann

  DOI：10.1002/chem.201804505

  日期：——

  highly‐defined synthetic scaffold. Herein, we present a new strategy for the versatile assembly of heteromultivalent glycomacromolecules that contain different carbohydrate motifs in proximity within the side chains. A new building block suitable for the solid‐phase polymer synthesis of precision glycomacromolecules was developed with a branching point in the side chain that bears a free alkyne and a TIPS‐protected

  通过在高度定义的合成支架上显示多个聚糖表位，精密糖大分子已被证明是研究多价碳水化合物-凝集素相互作用的重要工具。在本文中，我们提出了一种新的策略，用于杂合多价糖大分子的多功能组装，该杂多价糖大分子在侧链内附近包含不同的碳水化合物基序。开发了一种适用于精密糖大分子固相聚合物合成的新构件，其侧链上的支化点带有一个游离炔和一个TIPS保护的炔部分，这使得随后的不同碳水化合物基序可以通过on-树脂铜介导的叠氮化物-炔烃环加成反应。应用这种综合策略，
• Toward Orthogonal Preparation of Sequence-Defined Monodisperse Heteromultivalent Glycomacromolecules on Solid Support Using Staudinger Ligation and Copper-Catalyzed Click Reactions
  作者：Tanja Freichel、Svenja Eierhoff、Nicole L. Snyder、Laura Hartmann

  DOI：10.1021/acs.joc.7b01398

  日期：2017.9.15

  mimicking complex glycoligands on a variety of scaffolds, have become important tools for studying the role of carbohydrates in chemistry and biology. In this paper, we report on a new synthetic strategy for the preparation of monodisperse, sequence-defined glycooligomers or so-called precision glycomacromolecules based on solid phase oligomer synthesis and the Staudinger ligation. This strategy employs

  复杂糖配体和蛋白质异多价相互作用的研究对于理解重要的生物过程和开发基于碳水化合物的药物至关重要。通过在多种支架上模拟复杂的糖配体而衍生的合成糖模拟物已成为研究碳水化合物在化学和生物学中的作用的重要工具。在本文中，我们报告了一种基于固相低聚物合成和施陶丁格连接法制备单分散，序列定义的糖低聚物或所谓的精密糖大分子的新合成策略。该策略采用了一种固体支撑的合成方法，该方法使用了一种新型的羧基官能化结构单元，该结构单元具有施陶丁格在固体支撑物上连接所需要的功能性手柄。此外，
• Solid-Phase Synthesis of Asymmetrically Branched Sequence-Defined Poly/Oligo(amidoamines)
  作者：Felix Wojcik、Simone Mosca、Laura Hartmann

  DOI：10.1021/jo202561k

  日期：2012.5.4

  We present for the first time the synthesis of asymmetrically branched sequence-defined poly/oligo(amidoamines) (PAAs) using solid-phase synthesis with the capability of introducing diversity at the side chains. We introduce two new versatile (diethylenetriamine) building blocks for solid-phase synthesis bearing Fmoc/Boc and Fmoc/Alloc protecting groups expanding recently used Fmoc/Boc protecting group strategy for linear PAAs to an Fmoc/Alloc/Boc strategy. This allows for orthogonal on-resin cleavage of Fmoc and Alloc protecting groups during solid-phase synthesis of PAAs with backbones differing in chain length and sequence. With these structures we then demonstrate the potential for generating asymmetrical branching by automated multiple on-resin cleavage of Alloc protecting groups as well as the introduction of side chains varying in length and number. Such systems have high potential as nonviral vectors for gene delivery and will allow for more detailed studies on the correlation between the degree of branching of PAAs and their resulting biological properties.