(2R,3R)-3'-benzyloxy-4'',6''-dibenzyloxyflavan | 863237-48-3

• 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'-benzyloxy-4'',6''-dibenzyloxyflavan
• 英文别名: (2R,3R)-2-(3-benzyloxy-phenyl)-5,7-dibenzyloxy-chroman-3-ol；(2R,3R)-5,7-bis(phenylmethoxy)-2-(3-phenylmethoxyphenyl)-3,4-dihydro-2H-chromen-3-ol
• CAS: 863237-48-3
• 化学式: C₃₆H₃₂O₅
• 分子量: 544.647
• InChiKey: DSADSFXCLDFPSF-YYFXGUOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3'-benzyloxy-4'',6''-dibenzyloxyflavan 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 12.0h， 生成 [(2R,3R)-5,7-dihydroxy-2-(3-hydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
  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
• 作为产物：
  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 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 1.08h， 生成 (2R,3R)-3'-benzyloxy-4'',6''-dibenzyloxyflavan
  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

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.