(1R,2R)-3-(2,4-bis(benzyloxy)-6-hydroxyphenyl)-1-phenylpropane-1,2-diol | 1350895-93-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (1R,2R)-3-(2,4-bis(benzyloxy)-6-hydroxyphenyl)-1-phenylpropane-1,2-diol
• CAS: 1350895-93-0
• 化学式: C₂₉H₂₈O₅
• 分子量: 456.538
• InChiKey: KAVXMVNOXCBWDF-XRKRLSELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  34.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  79.15
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1R,2R)-3-(2,4-bis(benzyloxy)-6-hydroxyphenyl)-1-phenylpropane-1,2-diol 在 4-二甲氨基吡啶 、 4-甲基苯磺酸吡啶 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 67.42h， 生成 (2R,3R)-5,7-bis(benzyloxy)-2-phenylchroman-3-yl 3,4,5-tris(benzyloxy)benzoate
  参考文献：
  名称：

  Anti-staphylococcal activity and β-lactam resistance attenuating capacity of structural analogues of (−)-epicatechin gallate

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2011.09.116
• 作为产物：
  描述：

  4,6-dibenzyloxy-2-methoxymethyloxybenzaldehyde 在 盐酸 、 lithium aluminium tetrahydride 、 甲基磺酰胺 、 AD-mix β 、 溴 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三苯基膦 、 potassium hydroxide 、 儿萘酚硼烷 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 152.67h， 生成 (1R,2R)-3-(2,4-bis(benzyloxy)-6-hydroxyphenyl)-1-phenylpropane-1,2-diol
  参考文献：
  名称：

  Anti-staphylococcal activity and β-lactam resistance attenuating capacity of structural analogues of (−)-epicatechin gallate

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2011.09.116

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.