(+)-(2R,3R)-((2R,3S)-5,7-bis(benzyloxy)-2-(3',4'-bis(benzyloxy)phenyl)chroman-3-yl)-4-methyl-2,3-bis(benzyloxy)succinate

• 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)-((2R,3S)-5,7-bis(benzyloxy)-2-(3',4'-bis(benzyloxy)phenyl)chroman-3-yl)-4-methyl-2,3-bis(benzyloxy)succinate
• 英文别名: 1-O-[(2R,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-3-yl] 4-O-methyl (2R,3R)-2,3-bis(phenylmethoxy)butanedioate
• 化学式: C₆₂H₅₆O₁₁
• 分子量: 977.12
• InChiKey: ORRAZBRTVCHEPL-KVCZHOCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12
• 重原子数：
  73
• 可旋转键数：
  25
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (+)-(2R,3R)-((2R,3S)-5,7-bis(benzyloxy)-2-(3',4'-bis(benzyloxy)phenyl)chroman-3-yl)-4-methyl-2,3-bis(benzyloxy)succinate 在 甲醇 、 氢氧化钾 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以97.93%的产率得到(2R,3S)-5,7-二(苄氧基)-2-[3,4-二(苄氧基)苯基]-3-色满醇
  参考文献：
  名称：

  WO2007/2877

  摘要：

  公开号：
• 作为产物：
  描述：

  5,7,3',4'-Tetra-O-benzylcatechin 、 (2R,3R)-2,3-dibenzoyloxy-3-methoxycarbonylpropanoic acid 、 N,N'-二环己基碳二亚胺 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.4h， 以62%的产率得到(+)-(2R,3R)-((2R,3S)-5,7-bis(benzyloxy)-2-(3',4'-bis(benzyloxy)phenyl)chroman-3-yl)-4-methyl-2,3-bis(benzyloxy)succinate
  参考文献：
  名称：

  WO2007/2877

  摘要：

  公开号：

文献信息

• 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。
• PREPARATION OF (+)-CATECHIN, (-)-EPICATECHIN, (-)-CATECHIN, (+)-EPICATECHIN, AND THEIR 5,7,3',4'-TETRA-O-BENZYL ANALOGUES
  申请人：MARS, INCORPORATED

  公开号：EP1896443A1

  公开（公告）日：2008-03-12
• [EN] PREPARATION OF (+)-CATECHIN, (-)-EPICATECHIN, (-)-CATECHIN, (+)-EPICATECHIN, AND THEIR 5,7,3',4'-TETRA-O-BENZYL ANALOGUES<br/>[FR] PREPARATION DE (+)-CATECHINE, (-)-EPICATECHINE, (-)-CATECHINE, (+)-EPICATECHINE, ET ANALOGUES DE 5,7,3',4'-TETRA-O-BENZYLE
  申请人：MARS INC

  公开号：WO2007002877A1

  公开（公告）日：2007-01-04

  [EN] 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 (£)-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.
  [FR] L'invention concerne des procédés de préparation de mélanges racémiques de 5,7,3',4'-tétra-O-benzyl-(±)-catéchine et (±)-épicatéchine, qui consistent à: (I) condenser 2-hydroxy-4,6-bis(benzyloxy)-acétophénone et 3,4-bis(benzyloxy)benzaldéhyde, cycliser le composé obtenu, oxyder le composé obtenu; (II) dihydroxyler (E)-3-(3',4'-bis(benzyloxy)phényl)prop-2-ene-1-ol et réduire le 1,2-diol; ou (III) coupler 3,5-bis(benzyloxy)phénol avec (E)-3,5-bis(benzyloxy)-2-(3',4'-bis(benzyloxy)phényl)allyl)phénol et cycliser la chalcone obtenue. Par ailleurs, l'invention concerne un procédé de préparation des épimères benzylés de catéchine et d'épicatéchine, en sept étapes: 3,4-Bis(benzyloxy)benzaldéhyde est couplé à 2-hydroxy-4,6-benzyloxy-acétophénone pour former une chalcone. La chalcone est sélectivement réduite à un alcène. Le groupe phénolique de l'alcène est protégé. L'alcène protégé est asymétriquement dihydroxylé. Le composé obtenu est déprotégé, cyclisé, et enfin, hydrolysé. Les épimères résultant de ces procédés sont chimiquement séparés par chromatographie liquide à haute performance chirale. De plus, l'invention concerne un procédé de préparation de 5,7,3',4'-tétra-O-benzyl-(+)-catéchine énantiomériquement pure à partir d'un mélange racémique et en faisant intervenir de l'ester monométhylique d'acide dibenzoyl-L-tartarique. L'invention concerne enfin un procédé amélioré de préparation d'ester monométhylique d'acide dibenzoyl-L-tartarique.
• WO2007/2877
  申请人：——

  公开号：——

  公开（公告）日：——