1-azido-2-Fmoc-aminoethane | 432507-62-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 1-azido-2-Fmoc-aminoethane
• 英文别名: (9H-fluoren-9-yl)methyl (2-azidoethyl)carbamate；2-(Fmoc-amino)azidoethane；Fmoc-EDA-N3；9H-fluoren-9-ylmethyl N-(2-azidoethyl)carbamate
• CAS: 432507-62-5
• 化学式: C₁₇H₁₆N₄O₂
• 分子量: 308.34
• InChiKey: HIOHZKBHUFSLNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  52.7
• 氢给体数：
  1
• 氢受体数：
  4

制备方法与用途

Fmoc-EDA-N3是一种含有叠氮化物基团的点击化学试剂[1]。

反应信息

• 作为反应物：
  描述：

  1-azido-2-Fmoc-aminoethane 在 氯仿 、 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 生成 N-芴甲氧羰基乙二胺盐酸盐
  参考文献：
  名称：

  N-Urethane-Protected Amino Alkyl Isothiocyanates: Synthesis, Isolation, Characterization, and Application to the Synthesis of Thioureidopeptides

  摘要：

  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).

  DOI：

  10.1021/jo900675s
• 作为产物：
  描述：

  2-(N-芴甲氧羰基氨基)乙醇 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 1-azido-2-Fmoc-aminoethane
  参考文献：
  名称：

  微波无溶剂区选择性1,3偶极环加成反应，合成1,4取代的[1,2,3]-三唑为酰胺键等排体

  摘要：

  Fmoc-氨基叠氮化物和炔属酰胺的1,3偶极环加成反应在无溶剂辐射下产生1,4或1,5取代的[1,2,3]-三唑的混合物。碘化铜（I）的存在对区域选择性起着核心作用。四个Fmoc-氨基叠氮化物的特征在于侧链上的空间位阻不同，并且三个不同的末端炔烃在微波加热下仅提供1,4取代的区域异构体。产率高，有机溶剂消耗少，反应时间短是我们程序的主要方面。将反应与在室温下进行的区域选择性铜（I）催化的溶液合成进行比较。

  DOI：

  10.1002/jhet.5570440410

文献信息

• Sialic acid dimers
  申请人：Brossmer Reinhard

  公开号：US09260467B2

  公开（公告）日：2016-02-16

  Sialic acid derivatives of the formula (I) in which the symbols have the definitions stated in the description are suitable as medicaments, more particularly for diseases whose course is influenced by Siglec ligands.

  公式（I）中的唾液酸衍生物 其中符号的定义如描述中所述，适用作为药物，更具体地用于受Siglec配体影响的疾病。
• Synthesis of N-urethane protected amino alkyl (S-methyl)-isothiouronium compounds and carbodiimide tethered peptidomimetics: an application for guanidino and substituted guanidino peptidomimetics synthesis
  作者：Basavaprabhu Hosamani、N. Narendra、Girish Prabhu、Vommina V. Sureshbabu

  DOI：10.1039/c4ra07252a

  日期：——

  The synthesis of N,N′-disubstituted and N,N′,N′′-trisubstituted guanidine linked peptidomimetic molecules suitably decorated in the peptide backbone has been delineated. Nα-Protected amino acid derived S-methyl isothiouronium derivatives are employed as the key intermediates for the synthesis of guanidinopeptide mimics. Synthesis of a new class of carbodiimide tethered dipeptidomimetics has also been outlined wherein a Staudinger-aza-Wittig type reaction between amino alkyl azide and isothiocyanato esters is employed. Thus obtained carbodiimides have been demonstrated as starting materials for the construction of guanidino peptide mimics as well as an array of trisubstituted guanidine mimetics bearing N-hydroxy, cyano and amino function as third substitutions at the guanidino unit in the backbone.

  已阐明了合成N,N′-二取代和N,N′,N′′-三取代的胍基连接肽模仿分子，这些分子在肽骨架中进行了适当的装饰。采用Nα-保护的氨基酸衍生的S-甲基异硫脲盐衍生物作为合成胍基肽模仿物的关键中间体。还概述了一类新型的碳二亚胺连接的二肽模仿物的合成，其中采用氨基烷基叠氮化物与异硫氰酸酯之间的斯陶丁格-阿扎-维蒂格反应。因此获得的碳二亚胺已被证明是构建胍基肽模仿物的起始材料，以及一系列具有N-羟基、氰基和氨基作为胍基单元中第三取代基的三取代胍基模仿物。
• Tri-Orthogonal Scaffolds for the Solid-Phase Synthesis of Peptides
  作者：Jan Pícha、Benjamin Fabre、Miloš Buděšínský、Jan Hajduch、Mehdi Abdellaoui、Jiří Jiráček

  DOI：10.1002/ejoc.201800601

  日期：2018.10.9

  Three tripodal scaffolds were developed and tested for the step‐by‐step synthesis of three different peptides on the same scaffold by solid‐phase synthesis. Such compounds with three different peptides attached to a central core could mimic large proteins and find applications in modulating protein–protein interactions.

  开发了三个三脚架支架，并通过固相合成对同一支架上的三种不同肽的逐步合成进行了测试。这种在中央核心上带有三种不同肽的化合物可以模仿大蛋白，并在调节蛋白与蛋白的相互作用中找到应用。
• Late‐Stage Dehydroxyazidation of Alcohols Promoted by Trifunctional Hypervalent Azido‐Iodine(III) Reagents
  作者：Xiao‐Guang Yang、Feng‐Huan Du、Jun‐Jie Li、Chi Zhang

  DOI：10.1002/chem.202200272

  日期：2022.5.11

  We developed a mild, metal-free practical method for late-stage dehydroxyazidation of structurally complex alcohols promoted by trifunctional hypervalent azido-iodine(III) reagents ABZ. The reactions proceeded via an SN2 pathway and showed excellent chemoselectivity and stereospecificity and gave the corresponding azides in high yields. The reaction mechanism was investigated by means of experiments

  我们开发了一种温和、无金属的实用方法，用于由三官能高价叠氮碘 (III) 试剂 ABZ 促进的结构复杂醇的后期脱羟基叠氮化。该反应通过S N 2 途径进行，表现出优异的化学选择性和立体特异性，并以高收率得到相应的叠氮化物。通过实验和DFT计算研究了反应机理。
• A Facile One-Pot Synthesis of Selenoureidopeptides Employing LiAlHSeH through Staudinger Aza-Wittig-Type Reaction
  作者：Vommina Sureshbabu、Kupendra Sharanabai、Girish Prabhu、Veladi Panduranga

  DOI：10.1055/s-0034-1379638

  日期：——

  compounds that avoids the synthesis of isoselenocyanates and does not require multistep synthesis. A one-pot protocol for the synthesis of selenoureidopeptides employing lithium aluminum hydride hydroselenide (LiAlHSeH) as a selenating agent via a Staudinger aza-Wittig-type reaction is reported. The protocol involves the use of Nα-protected aminoalkyl azides and isothicyanato esters to afford the desired

  摘要 据报道，一锅法合成硒酸脲肽的方法是使用氢化锂铝氢化硒（LiAlHSeH）作为硒化剂，通过施陶丁格aza-Wittig型反应进行。该协议包括使用N个α -保护的氨基烷基叠氮化物和isothicyanato酯，得到以良好的收率的所需产物。该方案是合成硒代脲类化合物的直接方法，可避免合成异戊二烯酸酯，并且不需要多步合成。 据报道，一锅法合成硒酸脲肽的方法是使用氢化锂铝氢化硒（LiAlHSeH）作为硒化剂，通过施陶丁格aza-Wittig型反应进行。该协议包括使用N个α -保护的氨基烷基叠氮化物和isothicyanato酯，得到以良好的收率的所需产物。该方案是合成硒代脲类化合物的直接方法，可避免合成异戊二烯酸酯，并且不需要多步合成。