(Z)-N^α-benzyloxycarbonyl-Nⁱⁿ-tert-butyloxycarbonyl-2,3-dehydro-3-(indol-5'-yl)-alanine, methyl ester | 460096-32-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (Z)-N^α-benzyloxycarbonyl-Nⁱⁿ-tert-butyloxycarbonyl-2,3-dehydro-3-(indol-5'-yl)-alanine, methyl ester
• 英文别名: tert-butyl 5-[(Z)-3-methoxy-3-oxo-2-(phenylmethoxycarbonylamino)prop-1-enyl]indole-1-carboxylate
• CAS: 460096-32-6
• 化学式: C₂₅H₂₆N₂O₆
• 分子量: 450.491
• InChiKey: IWSAUGLNNQLZCE-HKWRFOASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  95.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Z)-N^α-benzyloxycarbonyl-Nⁱⁿ-tert-butyloxycarbonyl-2,3-dehydro-3-(indol-5'-yl)-alanine, methyl ester 在 (-)-1,2-双[(2R,5R)-2,5-二甲基磷]苯 氢气 作用下， 以 二氯甲烷 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 72.0h， 以100%的产率得到(R)-N^α-benzyloxycarbonyl-Nⁱⁿ-tert-butyloxycarbonyl-3-(indol-5'-yl)-alanine, methyl ester
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of Protected Tryptophan Regioisomers

  摘要：

  Tryptophan 1 (Trp) is superior to all other naturally occurring peptide residues in its ability to bind cations (the cation-a interaction). In an effort to expand the toolbox of Trp-like amino acids, in this note we report catalytic asymmetric syntheses of Trp regioisomers 2a-e, where the alanine unit is attached not to C-3 of indole but to C-2, C-4, C-5, C-6, or C-7. Excellent asymmetric induction is obtained in each case (generally >97% ee). Ab initio calculations suggest that the indole nuclei of 2a-e will bind Na+ with the same affinity as that of Trp.

  DOI：

  10.1021/jo025964i
• 作为产物：
  描述：

  5-吲哚甲醛 在 potassium tert-butylate 、 四甲基胍 作用下， 以 四氢呋喃 为溶剂， 反应 144.0h， 生成 (Z)-N^α-benzyloxycarbonyl-Nⁱⁿ-tert-butyloxycarbonyl-2,3-dehydro-3-(indol-5'-yl)-alanine, methyl ester
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of Protected Tryptophan Regioisomers

  摘要：

  Tryptophan 1 (Trp) is superior to all other naturally occurring peptide residues in its ability to bind cations (the cation-a interaction). In an effort to expand the toolbox of Trp-like amino acids, in this note we report catalytic asymmetric syntheses of Trp regioisomers 2a-e, where the alanine unit is attached not to C-3 of indole but to C-2, C-4, C-5, C-6, or C-7. Excellent asymmetric induction is obtained in each case (generally >97% ee). Ab initio calculations suggest that the indole nuclei of 2a-e will bind Na+ with the same affinity as that of Trp.

  DOI：

  10.1021/jo025964i

文献信息

• Catalytic Asymmetric Synthesis of Protected Tryptophan Regioisomers
  作者：Paul R. Carlier、Polo C.-H. Lam、Dawn M. Wong

  DOI：10.1021/jo025964i

  日期：2002.8.1

  Tryptophan 1 (Trp) is superior to all other naturally occurring peptide residues in its ability to bind cations (the cation-a interaction). In an effort to expand the toolbox of Trp-like amino acids, in this note we report catalytic asymmetric syntheses of Trp regioisomers 2a-e, where the alanine unit is attached not to C-3 of indole but to C-2, C-4, C-5, C-6, or C-7. Excellent asymmetric induction is obtained in each case (generally >97% ee). Ab initio calculations suggest that the indole nuclei of 2a-e will bind Na+ with the same affinity as that of Trp.