(S)-2-Acetylamino-3-[4-benzyloxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid methyl ester | 586968-83-4

• 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: (S)-2-Acetylamino-3-[4-benzyloxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid methyl ester
• CAS: 586968-83-4
• 化学式: C₂₅H₃₂BNO₆
• 分子量: 453.343
• InChiKey: JILAEUVCUCDVQN-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  83.09
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-acetamido-3-(3-iodo-4-phenylmethoxyphenyl)propanoate 、 (S)-2-Acetylamino-3-[4-benzyloxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid methyl ester 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium carbonate 、 联硼酸频那醇酯 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 生成 methyl (2S)-2-acetamido-3-[3-[5-[(2S)-2-acetamido-3-methoxy-3-oxopropyl]-2-phenylmethoxyphenyl]-4-phenylmethoxyphenyl]propanoate
  参考文献：
  名称：

  Synthesis of Dityrosine Cross-Linked Peptide Dimers Using the Miyaura−Suzuki Reaction

  摘要：

  GraphicsSince peroxidase-catalyzed dityrosine formation is inefficient for peptides, we have developed alternative conditions for intermolecular dityrosine formation using the Miyaura-Suzuki reaction. A one-pot reaction is effective for cross-linking short peptides, but longer peptides inhibit the Suzuki step, mandating a traditional two-step procedure using potassium acetate for the Miyaura reaction and potassium carbonate for the Suzuki coupling. These palladium-based methods are complementary to the well-established peroxidase-catalyzed oxidative phenolic coupling of full-length proteins.

  DOI：

  10.1021/ol034801t
• 作为产物：
  描述：

  methyl (S)-2-amino-3-(4-(benzyloxy)-3-iodophenyl)propanoate hydrochloride 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 (S)-2-Acetylamino-3-[4-benzyloxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid methyl ester
  参考文献：
  名称：

  Synthesis of Dityrosine Cross-Linked Peptide Dimers Using the Miyaura−Suzuki Reaction

  摘要：

  GraphicsSince peroxidase-catalyzed dityrosine formation is inefficient for peptides, we have developed alternative conditions for intermolecular dityrosine formation using the Miyaura-Suzuki reaction. A one-pot reaction is effective for cross-linking short peptides, but longer peptides inhibit the Suzuki step, mandating a traditional two-step procedure using potassium acetate for the Miyaura reaction and potassium carbonate for the Suzuki coupling. These palladium-based methods are complementary to the well-established peroxidase-catalyzed oxidative phenolic coupling of full-length proteins.

  DOI：

  10.1021/ol034801t