(1R,2R)-1-(3'-benzyloxyphenyl)-3-(2''-hydroxy-4'',6''-dibenzyloxyphenyl)propane-1,2-diol | 863237-46-1

• 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)-1-(3'-benzyloxyphenyl)-3-(2''-hydroxy-4'',6''-dibenzyloxyphenyl)propane-1,2-diol
• 英文别名: (1R,2R)-3-[2-hydroxy-4,6-bis(phenylmethoxy)phenyl]-1-(3-phenylmethoxyphenyl)propane-1,2-diol
• CAS: 863237-46-1
• 化学式: C₃₆H₃₄O₆
• 分子量: 562.662
• InChiKey: YMCLHKWFXUBPKU-QZCRLSDHSA-N

物化性质

• 熔点：
  120-122 °C
• 沸点：
  779.6±60.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,2R)-1-(3'-benzyloxyphenyl)-3-(2''-hydroxy-4'',6''-dibenzyloxyphenyl)propane-1,2-diol 在 乙酰溴 、 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 1.08h， 生成 Formic acid (1R,2S)-2-(3-benzyloxy-phenyl)-1-(2,4-bis-benzyloxy-6-hydroxy-benzyl)-2-bromo-ethyl ester
  参考文献：
  名称：

  Structure–activity study of epi-gallocatechin gallate (EGCG) analogs as proteasome inhibitors

  摘要：

  The structure-activity relationship of a number of synthetic green tea polyphenol analogs involving modifications of A ring and B ring of epi-gallocatechin gallate (EGCG) as proteasome inhibitors has been examined. It was found that in B ring, a decrease in the number of OH groups led to decreased potency. Introduction of a hydrophobic benzyl group into the 8 position of A ring did not significantly affect the proteasome-inhibitory potency. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.056
• 作为产物：
  描述：

  3-苄氧基苯乙酮 在 盐酸 、 氢氧化钾 、 sodium tetrahydroborate 、 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 、 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 144.0h， 生成 (1R,2R)-1-(3'-benzyloxyphenyl)-3-(2''-hydroxy-4'',6''-dibenzyloxyphenyl)propane-1,2-diol
  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

• US7700646B2
  申请人：——

  公开号：US7700646B2

  公开（公告）日：2010-04-20
• Asymmetric total synthesis of B-ring modified (−)-epicatechin gallate analogues and their modulation of β-lactam resistance in Staphylococcus aureus
  作者：James C. Anderson、Catherine Headley、Paul D. Stapleton、Peter W. Taylor

  DOI：10.1016/j.tet.2005.05.086

  日期：2005.8

  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.
• Structure–activity study of epi-gallocatechin gallate (EGCG) analogs as proteasome inhibitors
  作者：Sheng Biao Wan、Kristin R. Landis-Piwowar、Deborah J. Kuhn、Di Chen、Q. Ping Dou、Tak Hang Chan

  DOI：10.1016/j.bmc.2004.12.056

  日期：2005.3

  The structure-activity relationship of a number of synthetic green tea polyphenol analogs involving modifications of A ring and B ring of epi-gallocatechin gallate (EGCG) as proteasome inhibitors has been examined. It was found that in B ring, a decrease in the number of OH groups led to decreased potency. Introduction of a hydrophobic benzyl group into the 8 position of A ring did not significantly affect the proteasome-inhibitory potency. (c) 2005 Elsevier Ltd. All rights reserved.