(2R,3R)-7-(methoxymethoxy)-2-(4-methoxy-3-phenylmethoxyphenyl)-5-phenylmethoxy-3,4-dihydro-2H-chromen-3-ol | 1365537-14-9

• 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: (2R,3R)-7-(methoxymethoxy)-2-(4-methoxy-3-phenylmethoxyphenyl)-5-phenylmethoxy-3,4-dihydro-2H-chromen-3-ol
• CAS: 1365537-14-9
• 化学式: C₃₂H₃₂O₇
• 分子量: 528.602
• InChiKey: FFLYJHJQPKDZLH-WXGMZPBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,3R)-7-(methoxymethoxy)-2-(4-methoxy-3-phenylmethoxyphenyl)-5-phenylmethoxy-3,4-dihydro-2H-chromen-3-ol 在 盐酸 、 甲醇 、 sodium hydride 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 3.5h， 生成 (2R,3R)-2-(4-methoxy-3-phenylmethoxyphenyl)-3,5-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-7-ol
  参考文献：
  名称：

  A versatile approach to the regioselective synthesis of diverse (−)-epicatechin-β-d-glucuronides

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2012.01.054
• 作为产物：
  描述：

  1-(2-(benzyloxy)-4,6-dihydroxyphenyl)ethan-1-one 在 咪唑 、 甲醇 、 sodium tetrahydroborate 、 甲基磺酰胺 、 cerium(III) chloride heptahydrate 、 AD-mix-α 、 四丁基氟化铵 、 氨 、 水 、 4-甲基苯磺酸吡啶 、 aluminum isopropoxide 、 sodium hydride 、 戴斯-马丁氧化剂 、 溶剂黄146 、 N,N-二异丙基乙胺 、 异丙醇 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 、 叔丁醇 为溶剂， 反应 93.66h， 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：

  A versatile approach to the regioselective synthesis of diverse (−)-epicatechin-β-d-glucuronides

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2012.01.054

文献信息

• Enantioselective synthesis of orthogonally protected (2R,3R)-(−)-epicatechin derivatives, key intermediates in the de novo chemical synthesis of (−)-epicatechin glucuronides and sulfates
  作者：Mingbao Zhang、G. Erik Jagdmann、Michael Van Zandt、Paul Beckett、Hagen Schroeter

  DOI：10.1016/j.tetasy.2013.02.012

  日期：2013.4

  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.
• 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.
• Chemical Synthesis and Characterization of Epicatechin Glucuronides and Sulfates: Bioanalytical Standards for Epicatechin Metabolite Identification
  作者：Mingbao Zhang、G. Erik Jagdmann、Michael Van Zandt、Ryan Sheeler、Paul Beckett、Hagen Schroeter

  DOI：10.1021/np300568m

  日期：2013.2.22

  The monoglucuronides and sulfates of epicatechin, 3'-O-methylepicatechin, and 4'-O-methylepicatechin, respectively, were synthesized as authentic bioanalytical standards. Reversed-phase HPLC methods capable of baseline separation of the glucuronides and sulfates have been developed. Both the epicatechin glucuronides and sulfates were stable in the solid state when stored under ambient conditions and in aqueous solution when stored refrigerated. These results should prove invaluable to the research community as analytical standards as well as in future studies of the biological and pharmacological effects of epicatechin in humans.