methyl 2-(3-hydroxy-5-hydroxymethyl-2-methoxyphenoxy)-3,4,5-trimethoxybenzoate | 1242690-38-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: methyl 2-(3-hydroxy-5-hydroxymethyl-2-methoxyphenoxy)-3,4,5-trimethoxybenzoate
• 英文别名: Methyl 2-[3-hydroxy-5-(hydroxymethyl)-2-methoxyphenoxy]-3,4,5-trimethoxybenzoate
• CAS: 1242690-38-5
• 化学式: C₁₉H₂₂O₉
• 分子量: 394.378
• InChiKey: LBAKFYSPKWMXOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 2-(3-hydroxy-5-hydroxymethyl-2-methoxyphenoxy)-3,4,5-trimethoxybenzoate 在 咪唑 、 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 5-tert-butyldimethylsilyloxymethyl-2-methoxy-3-(2,3,4-trimethoxy-6-methoxycarbonylphenoxy)-phenyl-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 sodium tetrahydroborate 、 palladium 10% on activated carbon 、 氢气 、 铜 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~200.0 ℃ 、101.33 kPa 条件下， 反应 3.5h， 生成 methyl 2-(3-hydroxy-5-hydroxymethyl-2-methoxyphenoxy)-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

文献信息

• Synthesis of All-Methylated Isorugosin B
  作者：Kazuma Shioe、Yasuo Takeuchi、Takashi Harayama、Hitoshi Abe

  DOI：10.1248/cpb.58.435

  日期：——

  All-methylated isorugosin B was synthesized via two-step esterification between optically active valoneic acid and glucose derivatives.

  全甲基化异龙胆素 B 是通过光学活性丙酮酸和葡萄糖衍生物之间的两步酯化反应合成的。
• 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.