(R)-5-(benzyloxy)-2-(3-(benzyloxy)-4-methoxyphenyl)-7-(methoxymethoxy)chroman-3-one | 1365537-11-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (R)-5-(benzyloxy)-2-(3-(benzyloxy)-4-methoxyphenyl)-7-(methoxymethoxy)chroman-3-one
• CAS: 1365537-11-6
• 化学式: C₃₂H₃₀O₇
• 分子量: 526.586
• InChiKey: BHXDNEQQSTWGMY-JGCGQSQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.08
• 重原子数：
  39.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (R)-5-(benzyloxy)-2-(3-(benzyloxy)-4-methoxyphenyl)-7-(methoxymethoxy)chroman-3-one 在 aluminum isopropoxide 、 异丙醇 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 (2R,3R)-7-(methoxymethoxy)-2-(4-methoxy-3-phenylmethoxyphenyl)-5-phenylmethoxy-3,4-dihydro-2H-chromen-3-ol
  参考文献：
  名称：

  Enantioselective synthesis of orthogonally protected (2R,3R)-(−)-epicatechin derivatives, key intermediates in the de novo chemical synthesis of (−)-epicatechin glucuronides and sulfates

  摘要：

  Ten orthogonally protected (-)-epicatechin and 3'- or 4'-O-methyl-(-)-epicatechin derivatives were prepared in a regiospecific and enantioselective manner. For each orthogonally protected (-)-epicatechin derivative, one specific phenolic hydroxyl was protected with a methoxymethyl (MOM) or p-methoxybenyzl (PMB) group and the remainder were protected as benzyl ethers. These uniquely protected (-)-epicatechin derivatives were designed to facilitate the regiospecific installation of a glucuronic acid or sulfate unit onto (-)-epicatechin after selective removal of the MOM or PMB protecting group to provide authentic standards of (-)-epicatechin glucuronides and sulfates. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.02.012
• 作为产物：
  描述：

  (2R,3S)-5-(benzyloxy)-2-(3-(benzyloxy)-4-methoxyphenyl)-7-(methoxymethoxy)chroman-3-yl propionate 在 水 、 potassium carbonate 、 戴斯-马丁氧化剂 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 (R)-5-(benzyloxy)-2-(3-(benzyloxy)-4-methoxyphenyl)-7-(methoxymethoxy)chroman-3-one
  参考文献：
  名称：

  Enantioselective synthesis of orthogonally protected (2R,3R)-(−)-epicatechin derivatives, key intermediates in the de novo chemical synthesis of (−)-epicatechin glucuronides and sulfates

  摘要：

  Ten orthogonally protected (-)-epicatechin and 3'- or 4'-O-methyl-(-)-epicatechin derivatives were prepared in a regiospecific and enantioselective manner. For each orthogonally protected (-)-epicatechin derivative, one specific phenolic hydroxyl was protected with a methoxymethyl (MOM) or p-methoxybenyzl (PMB) group and the remainder were protected as benzyl ethers. These uniquely protected (-)-epicatechin derivatives were designed to facilitate the regiospecific installation of a glucuronic acid or sulfate unit onto (-)-epicatechin after selective removal of the MOM or PMB protecting group to provide authentic standards of (-)-epicatechin glucuronides and sulfates. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.02.012

文献信息

• A versatile approach to the regioselective synthesis of diverse (−)-epicatechin-β-d-glucuronides
  作者：Eric S. Mull、Michael Van Zandt、Adam Golebiowski、R. Paul Beckett、Pradeep K. Sharma、Hagen Schroeter

  DOI：10.1016/j.tetlet.2012.01.054

  日期：2012.3

  A versatile new approach is reported for the total synthesis of five glucuronide metabolites of epicatechin, using selective protection/deprotection techniques. (C) 2012 Elsevier Ltd. All rights reserved.