2S,2S-3-[2-(2-tert-butoxycarbonylamino-2-methoxycarbonylethyl)-phenyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid benzyl ester | 1011302-71-8

• 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: 2S,2S-3-[2-(2-tert-butoxycarbonylamino-2-methoxycarbonylethyl)-phenyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid benzyl ester
• 英文别名: methyl (2S)-3-[2-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-oxo-3-phenylmethoxypropyl]phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 1011302-71-8
• 化学式: C₄₀H₄₂N₂O₈
• 分子量: 678.782
• InChiKey: OOOAFPGVYVDBKG-PXLJZGITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  50
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2S,2S-3-[2-(2-tert-butoxycarbonylamino-2-methoxycarbonylethyl)-phenyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Synthesis of bis‐Phenylalanine, A Novel Eight‐Membered Cyclic Dipeptide

  摘要：

  Cyclic eight-membered ring lactams have been prepared which are formally analogs of Phe-Ala or Ala-Phe dipeptides joined together on their side chains. These are termed bis-phenylalanines because they are phenylalanine with respect to both of the residues in which the phenyl ring is shared between the two. The key synthetic step was the Negishi coupling of Boc-beta-I-Ala methyl ester with a suitably protected 2'-I phenylalanine.

  DOI：

  10.1080/00397910701771090
• 作为产物：
  描述：

  S-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(2-iodo-phenyl)-propionic acid benzyl ester 、 BOC-L-丙氨酸甲酯 在 二氯双(三邻甲苯膦)合钯(II) 碘 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.67h， 以47%的产率得到2S,2S-3-[2-(2-tert-butoxycarbonylamino-2-methoxycarbonylethyl)-phenyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid benzyl ester
  参考文献：
  名称：

  Synthesis of bis‐Phenylalanine, A Novel Eight‐Membered Cyclic Dipeptide

  摘要：

  Cyclic eight-membered ring lactams have been prepared which are formally analogs of Phe-Ala or Ala-Phe dipeptides joined together on their side chains. These are termed bis-phenylalanines because they are phenylalanine with respect to both of the residues in which the phenyl ring is shared between the two. The key synthetic step was the Negishi coupling of Boc-beta-I-Ala methyl ester with a suitably protected 2'-I phenylalanine.

  DOI：

  10.1080/00397910701771090

文献信息

• Synthesis of <i>bis</i>‐Phenylalanine, A Novel Eight‐Membered Cyclic Dipeptide
  作者：Brian V. Falcone、Christopher J. Creighton、Michael H. Parker、Allen B. Reitz

  DOI：10.1080/00397910701771090

  日期：2008.1.1

  Cyclic eight-membered ring lactams have been prepared which are formally analogs of Phe-Ala or Ala-Phe dipeptides joined together on their side chains. These are termed bis-phenylalanines because they are phenylalanine with respect to both of the residues in which the phenyl ring is shared between the two. The key synthetic step was the Negishi coupling of Boc-beta-I-Ala methyl ester with a suitably protected 2'-I phenylalanine.