(-)-(2S,3R)-trans-phenylflavan-3-yl-O-gallate | 1350895-89-4

• 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: (-)-(2S,3R)-trans-phenylflavan-3-yl-O-gallate
• 英文别名: [(2S,3R)-2-phenyl-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
• CAS: 1350895-89-4
• 化学式: C₂₂H₁₈O₆
• 分子量: 378.381
• InChiKey: CFGCVSCATFZPPH-CTNGQTDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-Flavanol, trans-(+)- 在 4-二甲氨基吡啶 、 10 wt% Pd(OH)2 on carbon 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 17.5h， 生成 (-)-(2S,3R)-trans-phenylflavan-3-yl-O-gallate
  参考文献：
  名称：

  Improved synthesis of structural analogues of (−)-epicatechin gallate for modulation of staphylococcal β-lactam resistance

  摘要：

  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.

  DOI：

  10.1016/j.tet.2014.03.052

文献信息

• Anti-staphylococcal activity and β-lactam resistance attenuating capacity of structural analogues of (−)-epicatechin gallate
  作者：James C. Anderson、Robert A. McCarthy、Sarah Paulin、Peter W. Taylor

  DOI：10.1016/j.bmcl.2011.09.116

  日期：2011.12

  We examined the impact of gradual removal of hydroxyl groups from the A- and B-rings of (-)-epicatechin gallate on antibacterial activity and oxacillin resistance attenuation of an epidemic strain of methicillin resistant Staphylococcus aureus. Removal of both hydroxyls from the B-ring effected a large reduction in oxacillin MIC (from 512 to 0.25 mg/mL at a concentration of 12.5 mg/L); further hydroxyl deletion of the A-ring reduced the oxacillin effect but increased intrinsic anti-staphylococcal activity (C) 2011 Elsevier Ltd. All rights reserved.
• 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.