4-(4-Benzyloxy-phenyl)-2-tert-butoxycarbonylamino-3-oxo-butyric acid methyl ester | 61172-72-3

• 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: 4-(4-Benzyloxy-phenyl)-2-tert-butoxycarbonylamino-3-oxo-butyric acid methyl ester
• CAS: 61172-72-3
• 化学式: C₂₃H₂₇NO₆
• 分子量: 413.47
• InChiKey: OCCFETNZDJUIGS-UHFFFAOYSA-N

物化性质

• 沸点：
  552.4±50.0 °C(Predicted)
• 密度：
  1.173±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  90.93
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-(4-Benzyloxy-phenyl)-2-tert-butoxycarbonylamino-3-oxo-butyric acid methyl ester 、 乙酸酐 生成 4-(4-Acetoxy-phenyl)-2-acetylamino-3-oxo-butyric acid methyl ester
  参考文献：
  名称：

  Stoffwechselprodukte von Mikroorganismen 159. Mitteilung.Über die aromatische Aminosäure des Echinocandins B: 3,4-Dihydroxyhomotyrosin

  摘要：

  The aromatic amino acid constituent of Echinocandin B: 3,4‐Dihydroxyhomotyrosine.The antifungal antibiotic echinocandin B gave upon treatment of its tetrahydroderivative with anhydrous trifluoroacetic acid and subsequent methanolysis the tripeptide threonyl‐(4‐hydroxyprolyl)‐(4‐oxohomotyrosine) methyl ester (8), which could be hydrolysed to 4‐oxohomotyrosine (11). These facts together with the earlier described hydrolysis of the antibiotic to 1‐amino‐3‐p‐hydroxyphenyl‐2‐propanone (6) and the reductive hydrolysis to homotyrosine suggested the presence of 3,4‐dihydroxyhomotyrosine (14) as a constituent amino acid of echinocandin B. This was confirmed by a degradation of the intact tetrahydro‐polypeptide with perjodate yielding p‐hydroxybenzaldehyde and by the isolation of free 3,4‐dihydroxyhomotyrosine upon mild acidic treatment of the tetrahydro‐polypeptide.

  DOI：

  10.1002/hlca.19760590615
• 作为产物：
  描述：

  N-重氮基氨基甲酸叔-丁基酯 生成 4-(4-Benzyloxy-phenyl)-2-tert-butoxycarbonylamino-3-oxo-butyric acid methyl ester
  参考文献：
  名称：

  Stoffwechselprodukte von Mikroorganismen 159. Mitteilung.Über die aromatische Aminosäure des Echinocandins B: 3,4-Dihydroxyhomotyrosin

  摘要：

  The aromatic amino acid constituent of Echinocandin B: 3,4‐Dihydroxyhomotyrosine.The antifungal antibiotic echinocandin B gave upon treatment of its tetrahydroderivative with anhydrous trifluoroacetic acid and subsequent methanolysis the tripeptide threonyl‐(4‐hydroxyprolyl)‐(4‐oxohomotyrosine) methyl ester (8), which could be hydrolysed to 4‐oxohomotyrosine (11). These facts together with the earlier described hydrolysis of the antibiotic to 1‐amino‐3‐p‐hydroxyphenyl‐2‐propanone (6) and the reductive hydrolysis to homotyrosine suggested the presence of 3,4‐dihydroxyhomotyrosine (14) as a constituent amino acid of echinocandin B. This was confirmed by a degradation of the intact tetrahydro‐polypeptide with perjodate yielding p‐hydroxybenzaldehyde and by the isolation of free 3,4‐dihydroxyhomotyrosine upon mild acidic treatment of the tetrahydro‐polypeptide.

  DOI：

  10.1002/hlca.19760590615

文献信息

• Stoffwechselprodukte von Mikroorganismen 159. Mitteilung.Über die aromatische Aminosäure des Echinocandins B: 3,4-Dihydroxyhomotyrosin
  作者：Walter Keller-Schierlein、Jörg Widmer

  DOI：10.1002/hlca.19760590615

  日期：——

  The aromatic amino acid constituent of Echinocandin B: 3,4‐Dihydroxyhomotyrosine.The antifungal antibiotic echinocandin B gave upon treatment of its tetrahydroderivative with anhydrous trifluoroacetic acid and subsequent methanolysis the tripeptide threonyl‐(4‐hydroxyprolyl)‐(4‐oxohomotyrosine) methyl ester (8), which could be hydrolysed to 4‐oxohomotyrosine (11). These facts together with the earlier described hydrolysis of the antibiotic to 1‐amino‐3‐p‐hydroxyphenyl‐2‐propanone (6) and the reductive hydrolysis to homotyrosine suggested the presence of 3,4‐dihydroxyhomotyrosine (14) as a constituent amino acid of echinocandin B. This was confirmed by a degradation of the intact tetrahydro‐polypeptide with perjodate yielding p‐hydroxybenzaldehyde and by the isolation of free 3,4‐dihydroxyhomotyrosine upon mild acidic treatment of the tetrahydro‐polypeptide.