N-<2-(p-Biphenylyl)-isopropyloxycarbonyl>-glycin-4-nitro-phenylester | 23650-18-2

• 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: N-<2-(p-Biphenylyl)-isopropyloxycarbonyl>-glycin-4-nitro-phenylester
• CAS: 23650-18-2
• 化学式: C₂₄H₂₂N₂O₆
• 分子量: 434.448
• InChiKey: JKEWEFHWAUUAPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.83
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  107.77
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-<2-(p-Biphenylyl)-isopropyloxycarbonyl>-glycin-4-nitro-phenylester 、 L-缬氨酸甲酯盐酸盐 在 N-甲基吗啉 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Bpoc-Gly-Val-OMe
  参考文献：
  名称：

  具有酸不稳定氨基保护基团的三氟乙醇中肽的选择性切割

  摘要：

  AbstractIn building up large polypeptides, it has become the established practice to use acide‐labile protecting groups of the t‐butyl type. Up to now, only one step of selectivity under acidic conditions has been used, consisting in the cleavage of Trt, Bpoc or Ppoc from N(α) without attacking the t‐butyl protecting groups. We have found that the use of 90% trifluoroethanol as solvent permits the selective cleavage of Trt in the presence of Bpoc or Ppoc under controlled acidolytic conditions. This additional selectivity‐step may be utilized when two‐chained polypeptides are to be constructed.The procedure consists in acidolytic cleavage with hydrochloric acid at a constant potential as measured by the glass electrode (pH‐stat). The automatic protonation of the freshly deprotected amino groups permits the evaluation of kinetic and quantitative data of the cleavage reaction. The selectivity ratios and cleavage conditions of Trt, Bpoc and Ppoc in N(α) are demonstrated here by reference to a series of model dipeptides. The successful application of this technique in the total synthesis of human insulin, a polypeptide with two peptida chains, has recently been described [8].

  DOI：

  10.1002/hlca.19750580412
• 作为产物：
  描述：

  1-(4-联苯基)-1-甲基乙基苯基碳酸酯 在 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 生成 N-<2-(p-Biphenylyl)-isopropyloxycarbonyl>-glycin-4-nitro-phenylester
  参考文献：
  名称：

  Über die Synthese von 2-(p-Biphenylyl)-isopropyloxycarbonyl-(Bpoc)-Aminosäuren und den Zerfall von Aralkyl-phenyl-carbonaten

  摘要：

  AbstractThe syntheses of a number of new Bpoc‐amino acids and the preparation of some activated esters of Bpoc‐amino acids are described. In recent work on the total synthesis of calcitonin hormones the Bpoc residue has been found to be very useful for the selective protection of α‐amino groups of complicated intermediate peptide fragments.The reagent preferentially used for the introduction of the Bpoc group into amino acids, [2‐(p‐biphenylyl)‐isopropyl]‐phenyl‐carbonate (I), is stable at 0°, but undergoes at higher temperatures a decomposition which is a accelerated by phenol. Based on the reaction products formed — [2‐(p‐biphenylyl)‐isopropyl]‐phenyl‐ether (II), 2‐(p‐biphenylyl)‐propene (III), and phenol — a scheme is proposed for this thermal decomposition, and the possibility of a correlation between the stability of carbonates R3C—O—CO—OC6H5 and the rate of the acidolytic cleavage of urethanes R3C—O—CO—NHR′ depending on the substituents R is discussed.

  DOI：

  10.1002/hlca.19690520613