methyl 4-O-tert-butyldimethylsilyl-2,3-di-O-(3,4,5-trimethoxybenzoyl)-α-D-glucopyranoside | 1242690-27-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: methyl 4-O-tert-butyldimethylsilyl-2,3-di-O-(3,4,5-trimethoxybenzoyl)-α-D-glucopyranoside
• 英文别名: [(2R,3R,4R,5R,6S)-3-[tert-butyl(dimethyl)silyl]oxy-2-(hydroxymethyl)-6-methoxy-5-(3,4,5-trimethoxybenzoyl)oxyoxan-4-yl] 3,4,5-trimethoxybenzoate
• CAS: 1242690-27-2
• 化学式: C₃₃H₄₈O₁₄Si
• 分子量: 696.821
• InChiKey: MWGRSZVFDPMTJL-QPZIMESWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  48
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  156
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  methyl 4-O-tert-butyldimethylsilyl-2,3-di-O-(3,4,5-trimethoxybenzoyl)-α-D-glucopyranoside 、 (S)-6'-tert-butyldimethylsilyloxymethyl-2,2',3,3',4-pentamethoxy-4'-(2,3,4-trimethoxy-6-methoxycarbonylphenoxy)-1,1'-biphenyl-6-carboxylic acid 在 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， 生成
  参考文献：
  名称：

  Synthesis of All-Methylated Isorugosin B

  摘要：

  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。

  DOI：

  10.1248/cpb.58.435
• 作为产物：
  描述：

  methyl 2,3-bis-O-(3,4,5-trimethoxybenzoyl)-α-D-glucopyranoside 在 2,6-二甲基吡啶 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 25.0h， 生成 methyl 4-O-tert-butyldimethylsilyl-2,3-di-O-(3,4,5-trimethoxybenzoyl)-α-D-glucopyranoside
  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.