(S)-4-[2-(9H-Fluoren-9-ylmethoxycarbonylamino)-phenyl]-2-hydroxy-butyric acid methyl ester | 192204-23-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (S)-4-[2-(9H-Fluoren-9-ylmethoxycarbonylamino)-phenyl]-2-hydroxy-butyric acid methyl ester
• 英文别名: methyl (2S)-4-[2-(9H-fluoren-9-ylmethoxycarbonylamino)phenyl]-2-hydroxybutanoate
• CAS: 192204-23-2
• 化学式: C₂₆H₂₅NO₅
• 分子量: 431.488
• InChiKey: MEJKRLIEOJIUEZ-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-4-[2-(9H-Fluoren-9-ylmethoxycarbonylamino)-phenyl]-2-hydroxy-butyric acid methyl ester 在 二甲基溴化硼 、 碘 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 68.33h， 生成 methyl (2S)-4-[2-(9H-fluoren-9-ylmethoxycarbonylamino)phenyl]-2-[(5-methyl-2,4-dioxopyrimidin-1-yl)methoxy]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：

  氯甲酸-9-芴基甲酯 、 (S)-4-(2-Amino-phenyl)-2-hydroxy-butyric acid methyl ester 在 sodium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.5h， 以84%的产率得到(S)-4-[2-(9H-Fluoren-9-ylmethoxycarbonylamino)-phenyl]-2-hydroxy-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.