(-)-(2R,3R)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate | 256236-30-3

• 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)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate
• 英文别名: (2R,3R)-5,7,3',4'-tetra-O-benzylflavan-3-yl (3'',4'',5''-tri-O-benzyl)gallate；[(2R,3R)-2-[3,4-bis(phenylmethoxy)phenyl]-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-tris(phenylmethoxy)benzoate
• CAS: 256236-30-3
• 化学式: C₇₁H₆₀O₁₀
• 分子量: 1073.25
• InChiKey: KWJCLAGWFCETNY-ULKDXPJMSA-N

物化性质

• 熔点：
  122-124 °C
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  15.3
• 重原子数：
  81
• 可旋转键数：
  25
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (-)-(2R,3R)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate 在 5% Pd(OH)₂/C 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 0.5h， 以98%的产率得到(-)-表儿茶素没食子酸酯
  参考文献：
  名称：

  General synthesis of epi-series catechins and their 3-gallates: reverse polarity strategy

  摘要：

  基于反极性策略，开发了一条合成表儿茶素类化合物的通用合成路线。通过芳香族亲核取代反应、亚磺酰基-金属交换及环化反应，实现了多种表儿茶素及其3-没食子酸酯的立体控制合成。

  DOI：

  10.1039/c003464a
• 作为产物：
  描述：

  3,4-二苄氧基苯甲醛 在 咪唑 、 4-二甲氨基吡啶 、 AD-mix-α 、 甲基磺酰胺 、 硫酸 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 silica gel 、 L-Selectride 、 sodium hydride 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 原甲酸三乙酯 作用下， 以 四氢呋喃 、 正己烷 、 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 15.0h， 生成 (-)-(2R,3R)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate
  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

• Synthesis of Bisflavanol-Type Natural Products and Their Analogues­ via Self-Coupling of C8-Methylol Catechin Derivatives
  作者：Deng-Ming Huang、Hui-Jing Li、Yan Zhao、Yan-Chao Wu

  DOI：10.1055/s-0037-1610707

  日期：2019.8

  acid-catalyzed catechin–formaldehyde condensation. A highly efficient and regioselective self-coupling of C8-methylol catechin derivatives is developed for the synthesis of dimeric flavanol analogues under metal-free and mild conditions. Its applicability is showcased by the efficient synthesis of bisflavanol-type natural products bis-8,8′-catechinylmethane, bis-8,8′-epicatechinylmethane, talienbisflavan A, and

  抽象的 为在无金属和温和条件下合成二聚黄烷醇类似物，开发了C8-羟甲基儿茶素衍生物的高效和区域选择性自偶联。双黄烷醇型天然产物bis-8,8'-儿茶素甲烷，bis-8,8'-表儿茶素甲烷，talienbisflavan A和oolonghomobisflavan A的有效合成证明了其适用性。新颖的自偶联机理为酸催化的儿茶素-甲醛缩合反应中的经典Friedel-Crafts烷基化机理。 为在无金属和温和条件下合成二聚黄烷醇类似物，开发了C8-羟甲基儿茶素衍生物的高效和区域选择性自偶联。双黄烷醇型天然产物bis-8,8'-儿茶素甲烷，bis-8,8'-表儿茶素甲烷，talienbisflavan A和oolonghomobisflavan A的有效合成证明了其适用性。新颖的自偶联机理为酸催化的儿茶素-甲醛缩合反应中的经典Friedel-Crafts烷基化机理。
• Asymmetric total synthesis of talienbisflavan A
  作者：Deng-Ming Huang、Hui-Jing Li、Jun-Hu Wang、Yan-Chao Wu

  DOI：10.1039/c7ob02837g

  日期：——

  The first asymmetric total syntheses of talienbisflavan A and bis-8,8′-epicatechinylmethane as well as a facile synthesis of bis-8,8′-catechinylmethane has been accomplished from readily available starting materials by using a newly developed direct regioselective methylenation of catechin derivatives as one of the key steps.

  talienbisflavan A和bis-8,8'-表儿茶素甲烷的第一个不对称全合成以及bis-8,8'-儿茶素甲烷的简便合成是通过使用新开发的儿茶素直接区域选择性甲基化技术从容易获得的原料中完成的衍生品作为关键步骤之一。
• Concise Synthesis of Procyanidin B2 3,3′′-Digallate Using Yb(OTf)3-Mediated Self-Condensation
  作者：Yuuri Tanaka、Shu-hei Kobayashi、Atsushi Kawamura、Hidefumi Makabe、Yasunao Hattori

  DOI：10.1055/s-0041-1737457

  日期：2022.7

  Lewis acid mediated self-condensation of epicatechin gallate derivative was examined. We found that Yb(OTf)3 afforded good yield of the dimeric epicatechin gallate derivative. The condensed product was applied to the synthesis of procyanidin B2 3,3′′-digallate.

  摘要 研究了刘易斯酸介导的表儿茶素没食子酸酯衍生物的自缩合。我们发现，Yb(OTf)3能提供较高产率的二聚表儿茶素没食子酸酯衍生物。缩合产物被用于合成原花青素 B2 3,3′′-二没食子酸酯。
• Synthesis of Galloyl-substituted Procyanidin B4 Series, and Their DPPH Radical Scavenging Activity and DNA Polymerase Inhibitory Activity
  作者：Noriyuki Nakajima、Hironori Sakuda、Akiko Saito、Yoshiyuki Mizushina、Hiromi Yoshida、Akira Tanaka

  DOI：10.3987/com-05-s(t)11

  日期：——
• Systematic synthesis of galloyl-substituted procyanidin B1 and B2, and their ability of DPPH radical scavenging activity and inhibitory activity of DNA polymerases
  作者：Akiko Saito、Yoshiyuki Mizushina、Hiroshi Ikawa、Hiromi Yoshida、Yuki Doi、Akira Tanaka、Noriyuki Nakajima

  DOI：10.1016/j.bmc.2005.02.023

  日期：2005.4

  Six galloyl-substituted procyanidin B1 and B2, 3-O-gallate, 3"-O-gallate, and 3,3"-di-O-gallate, were systematically synthesized with the condensation method using TMSOTf as a catalyst. Their ability of DPPH radical scavenging activity and DNA polymerase inhibitory activity were also investigated. The results indicated that the galloyl group of these compounds is very important for both activities. 3,3"-Di-O-gallate dimers acted as strong inhibitor against DNA polymerase alpha and beta, whereas the desgalloyl and monogalloyl compounds did not exhibit any appreciable inhibitory activity against the DNA polymerase beta. (c) 2005 Elsevier Ltd. All rights reserved.