methyl 6-O-methoxymethyl-2,3-di-O-(3,4,5-trimethoxybenzoyl)-α-D-glucopyranoside | 1278446-06-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-O-methoxymethyl-2,3-di-O-(3,4,5-trimethoxybenzoyl)-α-D-glucopyranoside
• CAS: 1278446-06-2
• 化学式: C₂₉H₃₈O₁₅
• 分子量: 626.612
• InChiKey: ISGKXQURELZYCG-NHAZSTSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.84
• 重原子数：
  44.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  165.13
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  (S)-6'-tert-butyldimethylsilyloxymethyl-2,2',3,3',4-pentamethoxy-4'-(2,3,4-trimethoxy-6-methoxycarbonylphenoxy)-1,1'-biphenyl-6-carboxylic acid 、 methyl 6-O-methoxymethyl-2,3-di-O-(3,4,5-trimethoxybenzoyl)-α-D-glucopyranoside 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， 以 二氯甲烷 为溶剂， 反应 24.0h， 以64%的产率得到
  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 2,3-bis-O-(3,4,5-trimethoxybenzoyl)-α-D-glucopyranoside 、 氯甲基甲基醚 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以80%的产率得到methyl 6-O-methoxymethyl-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