(-)-(2S,3R)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-ol | 87292-50-0

• 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)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-ol
• 英文别名: 5,7,3',4'-tetra-O-benzyl-(-)-catechin；(2S,3R)-2-[3,4-bis(phenylmethoxy)phenyl]-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-3-ol
• CAS: 87292-50-0
• 化学式: C₄₃H₃₈O₆
• 分子量: 650.771
• InChiKey: NRJRMFXLQSNZGY-HIJQYJRJSA-N

物化性质

• 熔点：
  136-138 °C
• 沸点：
  813.8±65.0 °C(Predicted)
• 密度：
  1.234±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 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：

  (-)-(2S,3R)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-ol 在 palladium(II) hydroxide/carbon 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、103.42 kPa 条件下， 反应 3.0h， 以84%的产率得到(-)-儿茶素
  参考文献：
  名称：

  WO2007/2877

  摘要：

  公开号：
• 作为产物：
  描述：

  (E)-3-(3,4-bis(benzyloxy)phenyl)prop-2-en-1-ol 在 咪唑 、 甲基磺酰胺 、 硫酸 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 silica gel 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 原甲酸三乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 9.0h， 生成 (-)-(2S,3R)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-ol
  参考文献：
  名称：

  Study of the green tea polyphenols catechin-3-gallate (CG) and epicatechin-3-gallate (ECG) as proteasome inhibitors

  摘要：

  The green tea polyphenol catechin-3-gallate (CG) and epicatechin-3-gallate (ECG) were synthesized enantioselectively via a Sharpless hydroxylation reaction followed by a diastereoselective cyclization. Their potencies to inhibit the proteasome activity were measured. The unnatural enantiomers were found to be equally potent to the natural compounds. (C) 2004 Elsevier Ltd, All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.033

文献信息

• Design, Synthesis <i>In Vitro</i> Anticancer Activity and Docking Studies of (−)‐Catechin Derivatives
  作者：Deepak Kumar、S. J. Harshavardhan、Sridhar Chirumarry、Y. Poornachandra、Kiwan Jang、C. Ganesh Kumar、Yong‐Jin Yoon、Bao‐Xiang Zhao、Jun‐Ying Miao、Dong‐Soo Shin

  DOI：10.1002/bkcs.10108

  日期：2015.2

  cytotoxicity against four selected human cancer cell lines by standard MTT assay method. Most of the compounds significantly active among which 1d exhibited promising activity with IC50 values of 2.5, 4.8 and 5.4 μM specifically against hepatocellular liver carcinoma (HepG2), lung adenocarcinoma (A549) and prostate (DU‐145) cell lines, while compound 1j showed promising cytotoxicity against human breast

  合成，表征新型系列（）-儿茶素衍生物1a-1，并通过标准MTT分析方法测定其对四种选定的人类癌细胞系的细胞毒性。大多数化合物具有显着活性，其中1d表现出良好的活性，IC 50值分别为2.5、4.8和5.4μM，特别是针对肝细胞肝癌（HepG2），肺腺癌（A549）和前列腺（DU-145）细胞系，而化合物1j对人乳腺腺癌MDA-MB-231具有良好的细胞毒性（IC 50值为6.6μM）。化合物1a，1d，1e，1f和1j对所有筛选的细胞系均表现出广谱细胞毒性。化合物1d的分子对接研究建立了良好的结合亲和力，有利于观察到的生物活性。这些数据共同表明，化合物1d可以作为进一步优化抗癌剂的新模板。
• Preparation of (+)-Catechin, (-)-Epicatechin, (-)-Catechin, and (+)-Epicatechin and Their 5,7,3',4'-Tetra-O-Benzyl Analogues
  申请人：Romanczyk, JR. Leo J.

  公开号：US20100048920A1

  公开（公告）日：2010-02-25

  Processes for preparing racemic mixtures of 5,7,3′,4′-tetra-O-benzyl-(±)-catechin and (±)-epicatechin involves (i) condensing 2-hydroxy-4,6-bis(benzyloxy)-acetophenone and 3,4-bis(benzyloxy)benzaldehyde, cyclizing the resulting compound, oxidizing the resulting compound; (ii) dihydroxylating (E)-3-(3′,4′-bis(benzyloxy)phenyl)prop-2-ene-1-ol and reducing the 1,2-diol; or (iii) coupling 3,5-bis(benzyloxy)phenol with (E)-3,5-bis(benzyloxy)-2-(3′,4′-bis(benzyloxy)phenyl)allyl)phenol and cyclizing the resulting chalcone. A process for preparing the benzylated epimers of catechin and epicatechin involves seven steps. 3,4-Bis(benzyloxy)benzaldehyde is coupled with 2-hydroxy-4,6-benzyloxy-acetophenone to form a chalcone. The chalcone is selectively reduced to an alkene. The phenolic group of the alkene is protected. The protected alkene is asymetrically dihydroxylated. The resulting compound is deprotected, cyclized, and finally hydrolyzed. Epimers resulting from these processes are chemically resolved or separated by chiral high pressure liquid chromatography. Also disclosed is a method for preparing enantiomerically pure 5,7,3′,4′-tetra-O-benzyl-(+)-catechin from a racemic mixture using dibenzoyl-L-tartaric acid monomethyl ester. Further, disclosed is an improved process for preparing dibenzoyl-L-tartaric acid monomethyl ester.

  制备5,7,3′,4′-四-O-苄基-(±)-儿茶素和(±)-表儿茶素的外消旋混合物的过程包括：(i)缩合2-羟基-4,6-双(苄氧基)-乙酮和3,4-双(苄氧基)苯甲醛，环化生成化合物，氧化化合物；(ii)双羟基化(E)-3-(3′,4′-双(苄氧基)苯基)丙-2-烯-1-醇，还原1,2-二醇；或(iii)将3,5-双(苄氧基)苯酚与(E)-3,5-双(苄氧基)-2-(3′,4′-双(苄氧基)苯基)丙烯基)苯酚偶联，生成的查尔酮环化。制备儿茶素和表儿茶素的苄基异构体的过程包括七个步骤。3,4-双(苄氧基)苯甲醛与2-羟基-4,6-双(苄氧基)-乙酮偶联形成查尔酮。查尔酮被选择性还原为烯烃。烯烃的酚基被保护。保护的烯烃被不对称地二羟基化。生成的化合物被去保护，环化，最后水解。这些过程生成的异构体通过手性高压液相色谱进行化学分离。还公开了一种使用二苯乙酰-L-酒石酸单甲酯制备对映纯5,7,3′,4′-四-O-苄基-(+)-儿茶素的方法。此外，还公开了一种改进的制备二苯乙酰-L-酒石酸单甲酯的方法。
• [EN] COMPOSITIONS AND METHODS FOR ANTIOXIDANT AND ANTI-INFLAMMATORY THERAPEUTICS<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR DES AGENTS THÉRAPEUTIQUES ANTIOXYDANTS ET ANTI-INFLAMMATOIRES
  申请人：[en]AVANTI BIOSCIENCES INC.

  公开号：WO2023288020A1

  公开（公告）日：2023-01-19

  The present invention relates to compositions and methods for antioxidant and anti-inflammatory therapeutics.
• Study of the green tea polyphenols catechin-3-gallate (CG) and epicatechin-3-gallate (ECG) as proteasome inhibitors
  作者：Sheng Biao Wan、Di Chen、Q. Ping Dou、Tak Hang Chan

  DOI：10.1016/j.bmc.2004.04.033

  日期：2004.7

  The green tea polyphenol catechin-3-gallate (CG) and epicatechin-3-gallate (ECG) were synthesized enantioselectively via a Sharpless hydroxylation reaction followed by a diastereoselective cyclization. Their potencies to inhibit the proteasome activity were measured. The unnatural enantiomers were found to be equally potent to the natural compounds. (C) 2004 Elsevier Ltd, All rights reserved.
• WO2007/2877
  申请人：——

  公开号：——

  公开（公告）日：——