(S)-4-{2-[(S)-4-(2-Amino-phenyl)-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethoxy)-butyrylamino]-phenyl}-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethoxy)-butyric acid methyl ester | 192204-31-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-4-{2-[(S)-4-(2-Amino-phenyl)-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethoxy)-butyrylamino]-phenyl}-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethoxy)-butyric acid methyl ester
• 英文别名: methyl (2S)-4-[2-[[(2S)-4-(2-aminophenyl)-2-[(5-methyl-2,4-dioxopyrimidin-1-yl)methoxy]butanoyl]amino]phenyl]-2-[(5-methyl-2,4-dioxopyrimidin-1-yl)methoxy]butanoate
• CAS: 192204-31-2
• 化学式: C₃₃H₃₈N₆O₉
• 分子量: 662.7
• InChiKey: UBWVINIBISWKJW-SVBPBHIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  48
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  199
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (S)-4-{2-[(S)-4-(2-Amino-phenyl)-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethoxy)-butyrylamino]-phenyl}-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethoxy)-butyric acid methyl ester 、 (S)-4-{2-[(S)-4-(2-tert-Butoxycarbonylamino-phenyl)-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethoxy)-butyrylamino]-phenyl}-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethoxy)-butyric acid 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以70%的产率得到methyl (2S)-2-[(5-methyl-2,4-dioxopyrimidin-1-yl)methoxy]-4-[2-[[(2S)-2-[(5-methyl-2,4-dioxopyrimidin-1-yl)methoxy]-4-[2-[[(2S)-2-[(5-methyl-2,4-dioxopyrimidin-1-yl)methoxy]-4-[2-[[(2S)-2-[(5-methyl-2,4-dioxopyrimidin-1-yl)methoxy]-4-[2-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]butanoyl]amino]phenyl]butanoyl]amino]phenyl]butanoyl]amino]phenyl]butanoate
  参考文献：
  名称：

  Stereoselective Synthesis of a Thymine Derivative of (S)-2-Hydroxy-4-(2-aminophenyl)butanoic Acid. A Novel Building Block for the Synthesis of Aromatic Peptidic Nucleic Acid Oligomers¹

  摘要：

  The synthesis of a thymine derivative of (S)-2-hydroxy-4-(2-aminophenyl)butanoic acid, compound 1, was achieved in high enantiomeric purity. The acyclic pyrimidine analog (S)-1 is a useful building block for the synthesis of a novel class of oligomers, the aromatic peptide nucleic acids (APNA, Scheme 1). The APNA tetramer 18 was prepared from the amino acid monomer (S)-1 using classical peptide synthesis. UV absorption spectra and H-1 NMR data of this tetramer suggested that base stacking interactions in the APNA oligomers may be favorable.

  DOI：

  10.1021/jo962326p
• 作为产物：
  描述：

  methyl (2S)-4-[2-(9H-fluoren-9-ylmethoxycarbonylamino)phenyl]-2-[(5-methyl-2,4-dioxopyrimidin-1-yl)methoxy]butanoate 在 哌啶 、 lithium hydroxide 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.58h， 生成 (S)-4-{2-[(S)-4-(2-Amino-phenyl)-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethoxy)-butyrylamino]-phenyl}-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethoxy)-butyric acid methyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of a Thymine Derivative of (S)-2-Hydroxy-4-(2-aminophenyl)butanoic Acid. A Novel Building Block for the Synthesis of Aromatic Peptidic Nucleic Acid Oligomers¹

  摘要：

  The synthesis of a thymine derivative of (S)-2-hydroxy-4-(2-aminophenyl)butanoic acid, compound 1, was achieved in high enantiomeric purity. The acyclic pyrimidine analog (S)-1 is a useful building block for the synthesis of a novel class of oligomers, the aromatic peptide nucleic acids (APNA, Scheme 1). The APNA tetramer 18 was prepared from the amino acid monomer (S)-1 using classical peptide synthesis. UV absorption spectra and H-1 NMR data of this tetramer suggested that base stacking interactions in the APNA oligomers may be favorable.

  DOI：

  10.1021/jo962326p

文献信息

• Stereoselective Synthesis of a Thymine Derivative of (<i>S</i>)-2-Hydroxy-4-(2-aminophenyl)butanoic Acid. A Novel Building Block for the Synthesis of Aromatic Peptidic Nucleic Acid Oligomers¹
  作者：Youla S. Tsantrizos、Jacqueline F. Lunetta、Michael Boyd、Lee D. Fader、Marie-Claire Wilson

  DOI：10.1021/jo962326p

  日期：1997.8.1

  The synthesis of a thymine derivative of (S)-2-hydroxy-4-(2-aminophenyl)butanoic acid, compound 1, was achieved in high enantiomeric purity. The acyclic pyrimidine analog (S)-1 is a useful building block for the synthesis of a novel class of oligomers, the aromatic peptide nucleic acids (APNA, Scheme 1). The APNA tetramer 18 was prepared from the amino acid monomer (S)-1 using classical peptide synthesis. UV absorption spectra and H-1 NMR data of this tetramer suggested that base stacking interactions in the APNA oligomers may be favorable.