benzyl 2-(benzyl{2-[(tert-butoxycarbonyl)amino]ethyl}amino)acetate | 174799-94-1

• 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: benzyl 2-(benzyl{2-[(tert-butoxycarbonyl)amino]ethyl}amino)acetate
• 英文别名: Benzyl 2-[Benzyl[2-(Boc-amino)ethyl]amino]acetate；benzyl 2-[benzyl-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]amino]acetate
• CAS: 174799-94-1
• 化学式: C₂₃H₃₀N₂O₄
• 分子量: 398.502
• InChiKey: VOLHBAAHYRYRCS-UHFFFAOYSA-N

物化性质

• 沸点：
  521.0±45.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl 2-(benzyl{2-[(tert-butoxycarbonyl)amino]ethyl}amino)acetate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以91.3%的产率得到([2-[(叔丁氧羰基)氨基]乙基]氨基)乙酸
  参考文献：
  名称：

  Building Units for N-Backbone Cyclic Peptides. 3. Synthesis of Protected N^α-(ω-Aminoalkyl)amino Acids and N^α-(ω-Carboxyalkyl)amino Acids

  摘要：

  An improved synthesis of a family of amino acids that contain omega-aminoalkyl groups and of a new family containing omega-carboxyalkyl groups linked to the alpha-amine is described. The synthesis was performed by alkylation of suitably monoprotected alkylenediamines and protected omega-amino acids with triflates of alpha-hydroxy acid esters. The reaction proceeded with inversion of configuration yielding optically pure products. The N-alpha-(omega-aminoalkyl)amino acids and N-alpha-(omega-carboxyalkyl)amino acids were orthogonally protected to allow their incorporation into peptides by solid-phase peptide synthesis (SPPS) methodology.

  DOI：

  10.1021/jo961580e
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 sodium tetrahydroborate 、 magnesium sulfate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 benzyl 2-(benzyl{2-[(tert-butoxycarbonyl)amino]ethyl}amino)acetate
  参考文献：
  名称：

  Building Units for N-Backbone Cyclic Peptides. 3. Synthesis of Protected N^α-(ω-Aminoalkyl)amino Acids and N^α-(ω-Carboxyalkyl)amino Acids

  摘要：

  An improved synthesis of a family of amino acids that contain omega-aminoalkyl groups and of a new family containing omega-carboxyalkyl groups linked to the alpha-amine is described. The synthesis was performed by alkylation of suitably monoprotected alkylenediamines and protected omega-amino acids with triflates of alpha-hydroxy acid esters. The reaction proceeded with inversion of configuration yielding optically pure products. The N-alpha-(omega-aminoalkyl)amino acids and N-alpha-(omega-carboxyalkyl)amino acids were orthogonally protected to allow their incorporation into peptides by solid-phase peptide synthesis (SPPS) methodology.

  DOI：

  10.1021/jo961580e

文献信息

• T-butoxycarbonylaminoethylamine for the Synthesis of PNA Monomer Units, Amino Acid Derivatives, Intermediates Thereof, and Processes for Productions of Them
  申请人：Ikeda Hisafumi

  公开号：US20080167491A1

  公开（公告）日：2008-07-10

  A process for amino acid derivatives shown by the below general formula (I): (wherein R 1 means a hydrogen atom or a straight chain or branched chain alkyl group with 1-5 carbon atoms.) having an object to provide a process of the amino acid derivatives of the formula (I) and their synthetic intermediate, t-butoxycarbonylamino-ethylamine, whereby it requires no tedious procedure and is also good in yield, and its application to a mass production is easy, and to provide novel amino acid derivatives of the formula (IV), their synthetic intermediates, and a process thereof, characterized in that it comprises a step to obtain the amino acid derivatives shown by the general formula (I) by hydrolysis of compounds shown by the below formula (II): (wherein R 1 has the same meaning as described above, and R 2 means a straight chain or branched chain alkyl group with 1-4 carbon atoms.) as well as amino acid derivatives shown by the general formula (IV): (wherein R 1 means a hydrogen atom or a straight chain or branched chain alkyl group with 1-5 carbon atoms, and n means any one of integers 1-11.), and a process for the amino acid derivative, characterized in that it comprises a reduction step of benzyloxycarbonyl-ω-amino acid derivatives.
• US7351852B2
  申请人：——

  公开号：US7351852B2

  公开（公告）日：2008-04-01
• Building Units for N-Backbone Cyclic Peptides. 3. Synthesis of Protected <i>N</i>^α-(ω-Aminoalkyl)amino Acids and <i>N</i>^α-(ω-Carboxyalkyl)amino Acids
  作者：Dan Muller、Irena Zeltser、Gal Bitan、Chaim Gilon

  DOI：10.1021/jo961580e

  日期：1997.1.1

  An improved synthesis of a family of amino acids that contain omega-aminoalkyl groups and of a new family containing omega-carboxyalkyl groups linked to the alpha-amine is described. The synthesis was performed by alkylation of suitably monoprotected alkylenediamines and protected omega-amino acids with triflates of alpha-hydroxy acid esters. The reaction proceeded with inversion of configuration yielding optically pure products. The N-alpha-(omega-aminoalkyl)amino acids and N-alpha-(omega-carboxyalkyl)amino acids were orthogonally protected to allow their incorporation into peptides by solid-phase peptide synthesis (SPPS) methodology.
• Synthesis of 5-Nitro-2-furancarbohydrazides and Their <i>cis</i>-Diamminedichloroplatinum Complexes as Bitopic and Irreversible Human Thioredoxin Reductase Inhibitors
  作者：Régis Millet、Sabine Urig、Judit Jacob、Eberhard Amtmann、Jacques-Philippe Moulinoux、Stephan Gromer、Katja Becker、Elisabeth Davioud-Charvet

  DOI：10.1021/jm050256l

  日期：2005.11.1

  The human selenoprotein thioredoxin reductase is involved in antioxidant defense and DNA synthesis. As increased thioredoxin reductase levels are associated with drug sensitivity to cisplatin and drug resistance in tumor cells, this enzyme represents a promising target for the development of cytostatic agents. To optimize the potential of the widely used cisplatin to inhibit the human thioredoxin reductase and therefore to overcome cisplatin resistance, we developed and synthesized four cis-diamminedichloroplatinum complexes of the lead 5-nitro-2-furan-carbohydrazide 8 selected from high-throughput screening. Detailed kinetics revealed that the isolated fragments, 5-nitro-2-furancarbohydrazide and cisplatin itself, bind with micromolar affinities at two different subsites of the human enzyme. By tethering both fragments four nitrofuran-based cis-diamminedichloroplatinum complexes 13a-c and 20 were synthesized and identified as biligand irreversible inhibitors of the human enzyme with nanomolar affinities. Studies with mutant enzymes clearly demonstrate the penultimate selenocysteine residue as the prime target of the synthesized cis-diamminedichloroplatinum complexes.