benzyl 5-(benzyloxy)-2-(S-cysteinyl)-3,4-dihydroxybenzoate | 169229-50-9

• 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: benzyl 5-(benzyloxy)-2-(S-cysteinyl)-3,4-dihydroxybenzoate
• 英文别名: (2R)-2-amino-3-(2,3-dihydroxy-4-phenylmethoxy-6-phenylmethoxycarbonylphenyl)sulfanylpropanoic acid
• CAS: 169229-50-9
• 化学式: C₂₄H₂₃NO₇S
• 分子量: 469.515
• InChiKey: RIJZSTXEOKUFDJ-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  165
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  benzyl 5-(benzyloxy)-2-(S-cysteinyl)-3,4-dihydroxybenzoate 在 钯 氢气 作用下， 以100%的产率得到2-(S-Cysteinyl)gallic acid
  参考文献：
  名称：

  Chemistry of Gallotannin-Derived o-Quinones: Reactivity toward Nucleophiles

  摘要：

  DOI：

  10.1021/jo00121a012
• 作为产物：
  描述：

  三乙酰基没食子酰氯 在 4-二甲氨基吡啶 、 邻四氯苯醌 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 potassium iodide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 丙酮 、 乙腈 为溶剂， 反应 51.5h， 生成 benzyl 5-(benzyloxy)-2-(S-cysteinyl)-3,4-dihydroxybenzoate
  参考文献：
  名称：

  Galloyl-Derived Orthoquinones as Reactive Partners in Nucleophilic Additions and Diels−Alder Dimerizations:  A Novel Route to the Dehydrodigalloyl Linker Unit of Agrimoniin-Type Ellagitannins

  摘要：

  Orthochloranil-mediated oxidation of galloyl monoethers furnishes the derived orthoquinones in excellent yield. These reactive electrophiles participate in a variety of nucleophilic addition reactions with heteroatomic and carbanionic partners. In addition, Lewis acid-mediated dimerization of the orthoquinones provides an efficient route to dehydrodigalloyl-type diaryl ether units characteristic of several ellagitannin natural products. The implications for ellagitannin biosynthesis and gallotannin-protein covalent attachment are discussed.

  DOI：

  10.1021/jo961043u

文献信息

• Chemistry of Gallotannin-Derived o-Quinones: Reactivity toward Nucleophiles
  作者：Stephane Quideau、Ken S. Feldman、Heidi M. Appel

  DOI：10.1021/jo00121a012

  日期：1995.8
• Galloyl-Derived Orthoquinones as Reactive Partners in Nucleophilic Additions and Diels−Alder Dimerizations:  A Novel Route to the Dehydrodigalloyl Linker Unit of Agrimoniin-Type Ellagitannins
  作者：Ken S. Feldman、Stéphane Quideau、Heidi M. Appel

  DOI：10.1021/jo961043u

  日期：1996.1.1

  Orthochloranil-mediated oxidation of galloyl monoethers furnishes the derived orthoquinones in excellent yield. These reactive electrophiles participate in a variety of nucleophilic addition reactions with heteroatomic and carbanionic partners. In addition, Lewis acid-mediated dimerization of the orthoquinones provides an efficient route to dehydrodigalloyl-type diaryl ether units characteristic of several ellagitannin natural products. The implications for ellagitannin biosynthesis and gallotannin-protein covalent attachment are discussed.