(2R,3R)-3',5'-dibenzyloxy-4'',6''-dibenzyloxyflavan | 863237-55-2

• 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)-3',5'-dibenzyloxy-4'',6''-dibenzyloxyflavan
• 英文别名: (2R,3R)-2-(3,5-bis-benzyloxy-phenyl)-5,7-dibenzyloxy-chroman-3-ol；(2R,3R)-5,7-bis(benzyloxy)-2-(3,5-bis(benzyloxy)phenyl)chroman-3-ol；(2R,3R)-2-[3,5-bis(phenylmethoxy)phenyl]-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-3-ol
• CAS: 863237-55-2
• 化学式: C₄₃H₃₈O₆
• 分子量: 650.771
• InChiKey: UZNAYURKHWPBBI-RCDGGPPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  49
• 可旋转键数：
  13
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3',5'-dibenzyloxy-4'',6''-dibenzyloxyflavan 在 palladium hydroxide 10 wt. % on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以94%的产率得到(2R,3R)-3,5,7,3',5'-pentahydroxyflavan
  参考文献：
  名称：

  Enantio Selective Synthesis of New Phenylpropanoid: Isolated from Walsura trifoliata

  摘要：

  从传统药用植物Walsura trifoliata的叶中分离出一种含有黄酮-3-醇的新苯丙烷类化合物。该化合物的结构是基于光谱证据[2D NMR，HREIMS]和其替代合成确定的。这种天然产物的合成是从廉价且易得的起始材料邻苯三酚二水合物中实现的。关键反应序列包括Grubbs-II RCM反应，Wittig反应和利用AD-mix α的Sharpless二羟基化反应。

  DOI：

  10.14233/ajchem.2019.22064
• 作为产物：
  描述：

  Formic acid (1R,2S)-1-(2,4-bis-benzyloxy-6-hydroxy-benzyl)-2-(3,5-bis-benzyloxy-phenyl)-2-bromo-ethyl ester 在 potassium carbonate 作用下， 以 丙酮 、 甲醇 为溶剂， 反应 5.0h， 以222 mg的产率得到(2R,3R)-3',5'-dibenzyloxy-4'',6''-dibenzyloxyflavan
  参考文献：
  名称：

  Asymmetric total synthesis of B-ring modified (−)-epicatechin gallate analogues and their modulation of β-lactam resistance in Staphylococcus aureus

  摘要：

  Two enantiomerically pure B-ring modified analogues of (-)epicatechin gallate were synthesised and their modulation of beta-lactam resistance using three strains of methicillin resistant Staphylococcus aureus (BB 568, EMRSA-15 and EMRSA-16) evaluated. Sub-inhibitory concentrations (12.5 and 25 mg/L) of the two analogues fully sensitised each of the three MRSA strains to oxacillin, reducing the MIC to less than 0.5 mg/L, identical to levels achieved with ECg. Lower concentrations demonstrated that the position and degree of hydroxylation of the B-ring is important for activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.05.086

文献信息

• Improved synthesis of structural analogues of (−)-epicatechin gallate for modulation of staphylococcal β-lactam resistance
  作者：James C. Anderson、Helen Grounds、Suzanna Reeves、Peter W. Taylor

  DOI：10.1016/j.tet.2014.03.052

  日期：2014.5

  The high-yielding synthesis of enantiomerically pure epicatechin gallate analogues where the A and/or B-ring hydroxylation is reduced or altered has been achieved by optimising routes to the catechin stereochemistry. The B-ring analogues were synthesised by using an electrophilic ring closure onto an enantiomerically enriched epoxide as a key step. The A and B-ring hydroxyl-deleted analogues were synthesised through a Mitsunobu cyclisation. For the B-ring analogues, the anti- (catechin) stereochemistry was converted to the syn- (epicatechin) stereochemistry by a known oxidation/reduction protocol. Absolute stereochemistry was derived from either a Sharpless epoxidation or asymmetric dihydroxylation. (C) 2014 The Authors. Published by Elsevier Ltd. All rights reserved.