3-benzyloxy-5,6'-bis(acetoxymethyl)-2,2',3',4'-tetramethoxy-1,1'-diphenylether | 1010094-03-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: 3-benzyloxy-5,6'-bis(acetoxymethyl)-2,2',3',4'-tetramethoxy-1,1'-diphenylether
• 英文别名: [3-[6-(Acetyloxymethyl)-2,3,4-trimethoxyphenoxy]-4-methoxy-5-phenylmethoxyphenyl]methyl acetate
• CAS: 1010094-03-7
• 化学式: C₂₉H₃₂O₁₀
• 分子量: 540.567
• InChiKey: VMHLYSPOKRRMLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-benzyloxy-5,6'-bis(acetoxymethyl)-2,2',3',4'-tetramethoxy-1,1'-diphenylether 在 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 17.0h， 生成 5-(acetoxymethyl)-3-(6-(acetoxymethyl)-2,3,4-trimethoxyphenoxy)-2-methoxyphenyl 2-iodo-3,4,5-trimethoxybenzoate
  参考文献：
  名称：

  Syntheses of all-methylated ellagitannin, isorugosin B and rugosin B

  摘要：

  Ellagitannins possess a wide range of biological activities and remarkable structural diversity, which commonly include an axially chiral biaryl unit. This paper describes syntheses of all-methylated versions of isorugosin B and rugosin B, which are regioisomeric, ellagitannin-related compounds. The key features of these syntheses involve the construction of an axially chiral biaryl function on a sugar moiety through a Pd-catalyzed intramolecular biaryl coupling reaction, Bringmann's atroposelective lactone opening reaction, and a two-step ester formation. This is the first synthetic approach for generating ellagitannins featuring a valoneoyl group. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.004
• 作为产物：
  描述：

  methyl 2-bromo-3,4,5-trimethoxybenzoate 在 吡啶 、 lithium aluminium tetrahydride 、 铜 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 3-benzyloxy-5,6'-bis(acetoxymethyl)-2,2',3',4'-tetramethoxy-1,1'-diphenylether
  参考文献：
  名称：

  Syntheses of all-methylated ellagitannin, isorugosin B and rugosin B

  摘要：

  Ellagitannins possess a wide range of biological activities and remarkable structural diversity, which commonly include an axially chiral biaryl unit. This paper describes syntheses of all-methylated versions of isorugosin B and rugosin B, which are regioisomeric, ellagitannin-related compounds. The key features of these syntheses involve the construction of an axially chiral biaryl function on a sugar moiety through a Pd-catalyzed intramolecular biaryl coupling reaction, Bringmann's atroposelective lactone opening reaction, and a two-step ester formation. This is the first synthetic approach for generating ellagitannins featuring a valoneoyl group. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.004

文献信息

• Enantioselective synthesis of valoneic acid derivative
  作者：Hitoshi Abe、Yusuke Sahara、Yuki Matsuzaki、Yasuo Takeuchi、Takashi Harayama

  DOI：10.1016/j.tetlet.2007.11.154

  日期：2008.1

  The enantioselective synthesis of trimethyl octa-O-methylvaloneate (1) was accomplished using the Bringniann's 'lactone concept', which involves the intramolecular biaryl coupling reaction of a phenyl benzoate derivative and the asymmetric lactone-opening reaction. (c) 2007 Elsevier Ltd. All rights reserved.
• Syntheses of all-methylated ellagitannin, isorugosin B and rugosin B
  作者：Kazuma Shioe、Yusuke Sahara、Yoshikazu Horino、Takashi Harayama、Yasuo Takeuchi、Hitoshi Abe

  DOI：10.1016/j.tet.2011.01.004

  日期：2011.3

  Ellagitannins possess a wide range of biological activities and remarkable structural diversity, which commonly include an axially chiral biaryl unit. This paper describes syntheses of all-methylated versions of isorugosin B and rugosin B, which are regioisomeric, ellagitannin-related compounds. The key features of these syntheses involve the construction of an axially chiral biaryl function on a sugar moiety through a Pd-catalyzed intramolecular biaryl coupling reaction, Bringmann's atroposelective lactone opening reaction, and a two-step ester formation. This is the first synthetic approach for generating ellagitannins featuring a valoneoyl group. (C) 2011 Elsevier Ltd. All rights reserved.