rac-2-{[(tert-butyloxy)carbonyl]amino}-3-(2'-methylbiphenyl-4-yl)propionic acid

• 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: rac-2-{[(tert-butyloxy)carbonyl]amino}-3-(2'-methylbiphenyl-4-yl)propionic acid
• 英文别名: Boc-4-(2-methylphenyl)-DL-phenylalanine；3-[4-(2-methylphenyl)phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• 化学式: C₂₁H₂₅NO₄
• 分子量: 355.434
• InChiKey: WZYJCLIFAJVGLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对溴苯丙氨酸 在 potassium phosphate 、 bis(η3-allyl-μ-chloropalladium(II)) 、 triethylammonium 2-(dicyclohexylphosphino)-4'-{[(sulfonatomethyl)amino]carbonyl}biphenyl 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 生成 rac-2-{[(tert-butyloxy)carbonyl]amino}-3-(2'-methylbiphenyl-4-yl)propionic acid
  参考文献：
  名称：

  Synthesis of an amidosulfonate-tagged biphenyl phosphine and its application in the Suzuki–Miyaura reaction affording biphenyl-substituted amino acids in water

  摘要：

  An amidosulfonate-tagged phosphinobiphenyl, viz triethylammonium 2-(dicyclohexylphosphino)-4'-{[(sulfonatomethyl)amino]carbonyl}biphenyl(3), was prepared in two steps from 2-(dicyclohexylphosphino) biphenyl-4'-carboxylic acid and fully characterized including the crystal structure determination. As a highly polar phosphine ligand, compound 3 was employed in the Pd-catalyzed Suzuki-Miyaura cross-coupling of N-Boc protected 4-bromo and 4-chlorophenylalanine with aromatic boronic acids to afford the corresponding biphenyls in aqueous N,N-dimethylformamide or pure water. The coupling was demonstrated to proceed very well and without the loss of the Boc protecting group when the bromo-substituted substrate is reacted in the presence of 1 mol.% of Pd/3 catalyst in water at 40 degrees C. Reactions with boronic acids bearing electron-withdrawing substituents and, mainly, those with the less reactive chlorophenylalanine substrate required slightly higher reaction temperature and more catalyst to achieve similar results. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2015.01.020

文献信息

• HUMAN GLUCAGON-LIKE PEPTIDE-1 MIMICS AND THEIR USE IN THE TREATMENT OF DIABETES AND RELATED CONDITIONS
  申请人：Natarajan Iyer Sesha

  公开号：US20070287670A1

  公开（公告）日：2007-12-13

  The present invention provides novel human glucagon-like peptide-1 (GLP-1) peptide mimics that mimic the biological activity of the native GLP-1 peptide and thus are useful for the treatment or prevention of diseases or disorders associated with GLP activity. Further, the present invention provides novel, chemically modified peptides that not only stimulate insulin secretion in type II diabetics, but also produce other beneficial insulinotropic responses. These synthetic peptide GLP-1 mimics exhibit increased stability to proteolytic cleavage making them ideal therapeutic candidates for oral or parenteral administration.

  本发明提供了新型的人类胰高血糖素样肽-1 (GLP-1) 肽类模拟物，这些模拟物模仿了天然的 GLP-1 肽的生物活性，因此可用于治疗或预防与 GLP 活性相关的疾病或疾病。此外，本发明提供了新型的化学修饰肽，这些肽不仅可以刺激 II 型糖尿病患者的胰岛素分泌，还可以产生其他有益的胰岛素促进反应。这些合成的 GLP-1 模拟物肽类表现出对蛋白酶水解的稳定性增加，使它们成为口服或静脉注射治疗的理想候选药物。
• US7238670B2
  申请人：——

  公开号：US7238670B2

  公开（公告）日：2007-07-03
• US7238671B2
  申请人：——

  公开号：US7238671B2

  公开（公告）日：2007-07-03
• Synthesis of an amidosulfonate-tagged biphenyl phosphine and its application in the Suzuki–Miyaura reaction affording biphenyl-substituted amino acids in water
  作者：Jiří Schulz、Ivana Císařová、Petr Štěpnička

  DOI：10.1016/j.jorganchem.2015.01.020

  日期：2015.11

  An amidosulfonate-tagged phosphinobiphenyl, viz triethylammonium 2-(dicyclohexylphosphino)-4'-[(sulfonatomethyl)amino]carbonyl}biphenyl(3), was prepared in two steps from 2-(dicyclohexylphosphino) biphenyl-4'-carboxylic acid and fully characterized including the crystal structure determination. As a highly polar phosphine ligand, compound 3 was employed in the Pd-catalyzed Suzuki-Miyaura cross-coupling of N-Boc protected 4-bromo and 4-chlorophenylalanine with aromatic boronic acids to afford the corresponding biphenyls in aqueous N,N-dimethylformamide or pure water. The coupling was demonstrated to proceed very well and without the loss of the Boc protecting group when the bromo-substituted substrate is reacted in the presence of 1 mol.% of Pd/3 catalyst in water at 40 degrees C. Reactions with boronic acids bearing electron-withdrawing substituents and, mainly, those with the less reactive chlorophenylalanine substrate required slightly higher reaction temperature and more catalyst to achieve similar results. (C) 2015 Elsevier B.V. All rights reserved.