[(2R,3R,4R,5S)-4-(3,5-dihydroxy-4-phenylmethoxybenzoyl)oxy-2-[(4-methoxyphenyl)methoxy]-3,5-bis(phenylmethoxy)hept-6-enyl] 3,5-dihydroxy-4-phenylmethoxybenzoate | 1034343-23-1

• 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: [(2R,3R,4R,5S)-4-(3,5-dihydroxy-4-phenylmethoxybenzoyl)oxy-2-[(4-methoxyphenyl)methoxy]-3,5-bis(phenylmethoxy)hept-6-enyl] 3,5-dihydroxy-4-phenylmethoxybenzoate
• CAS: 1034343-23-1
• 化学式: C₅₇H₅₄O₁₄
• 分子量: 963.047
• InChiKey: WUBSLRGAHKQAKM-DHOAXABWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  71
• 可旋转键数：
  27
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  189
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,5S)-4-(3,5-dihydroxy-4-phenylmethoxybenzoyl)oxy-2-[(4-methoxyphenyl)methoxy]-3,5-bis(phenylmethoxy)hept-6-enyl] 3,5-dihydroxy-4-phenylmethoxybenzoate 在 正丁胺 、 copper dichloride 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以76%的产率得到(10R,11R,12R)-3,5,18,20-tetrahydroxy-12-[(4-methoxyphenyl)methoxy]-4,11,19-tris(phenylmethoxy)-10-[(1S)-1-phenylmethoxyprop-2-enyl]-9,14-dioxatricyclo[14.4.0.02,7]icosa-1(20),2,4,6,16,18-hexaene-8,15-dione
  参考文献：
  名称：

  Total Synthesis of (−)-Corilagin

  摘要：

  The synthesis of corilagin was achieved by the integration of the development of the oxidative coupling of the symmetrically protected gallates and the temporarily ring-opened synthetic route for the 3.6-hexahydroxydiphenoyl (HHDP) bridge. This is the first total synthesis of the C-1(4)/B-ellagitannins, which contain ring-flipped glucose.

  DOI：

  10.1021/ja803111z
• 作为产物：
  描述：

  在 盐酸 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 12.0h， 以86%的产率得到[(2R,3R,4R,5S)-4-(3,5-dihydroxy-4-phenylmethoxybenzoyl)oxy-2-[(4-methoxyphenyl)methoxy]-3,5-bis(phenylmethoxy)hept-6-enyl] 3,5-dihydroxy-4-phenylmethoxybenzoate
  参考文献：
  名称：

  Total Synthesis of (−)-Corilagin

  摘要：

  The synthesis of corilagin was achieved by the integration of the development of the oxidative coupling of the symmetrically protected gallates and the temporarily ring-opened synthetic route for the 3.6-hexahydroxydiphenoyl (HHDP) bridge. This is the first total synthesis of the C-1(4)/B-ellagitannins, which contain ring-flipped glucose.

  DOI：

  10.1021/ja803111z

文献信息

• Total Synthesis of (−)-Corilagin
  作者：Hidetoshi Yamada、Kohei Nagao、Kazutoyo Dokei、Yusuke Kasai、Naoki Michihata

  DOI：10.1021/ja803111z

  日期：2008.6.18

  The synthesis of corilagin was achieved by the integration of the development of the oxidative coupling of the symmetrically protected gallates and the temporarily ring-opened synthetic route for the 3.6-hexahydroxydiphenoyl (HHDP) bridge. This is the first total synthesis of the C-1(4)/B-ellagitannins, which contain ring-flipped glucose.