(2R,3R,4S)-3-acetoxy-4-ethoxyethoxy-5,7-3',4',5'-pentabenzyloxyflavan | 1401236-90-5

• 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,4S)-3-acetoxy-4-ethoxyethoxy-5,7-3',4',5'-pentabenzyloxyflavan
• 英文别名: [(2R,3R,4S)-4-(2-ethoxyethoxy)-5,7-bis(phenylmethoxy)-2-[3,4,5-tris(phenylmethoxy)phenyl]-3,4-dihydro-2H-chromen-3-yl] acetate
• CAS: 1401236-90-5
• 化学式: C₅₆H₅₄O₁₀
• 分子量: 887.039
• InChiKey: WZHZMTYPJANANS-OKPMFDBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  66
• 可旋转键数：
  23
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.23
• 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,4S)-3-acetoxy-4-ethoxyethoxy-5,7-3',4',5'-pentabenzyloxyflavan 在 zinc trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以59%的产率得到[4,8′]-2,3-cis-3,4-trans:2′,3′-cis-dodeca-o-benzyl-3,3′-o-diacetyl-4′-(2-ethoxyethoxy)bi-(-)-epigallocatechin
  参考文献：
  名称：

  三氟甲磺酸锌（II）介导的自缩合选择性合成表儿茶素二聚体

  摘要：

  摘要 表儿茶素二聚体是通过三氟甲磺酸锌（II）介导的表儿茶素单体衍生物的自缩合反应合成的。一种合成的二聚体成功转化为原花青素C1。 表儿茶素二聚体是通过三氟甲磺酸锌（II）介导的表儿茶素单体衍生物的自缩合反应合成的。一种合成的二聚体成功转化为原花青素C1。

  DOI：

  10.1055/s-0034-1378998
• 作为产物：
  描述：

  (2R,3R,4S)-3-acetoxy-4-ethoxyethoxy-5,7-3',4',5'-pentabenzyloxyflavan 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以7.3 g的产率得到(2R,3R,4S)-3-acetoxy-4-ethoxyethoxy-5,7-3',4',5'-pentabenzyloxyflavan
  参考文献：
  名称：

  Unified approach to catechin hetero-oligomers: first total synthesis of trimer EZ–EG–CA isolated from Ziziphus jujuba

  摘要：

  我们合成了一种从紫竹中分离出来的儿茶素杂三聚体。在三个组成单体中，(§)-表儿茶素和(§)-表没食子儿茶素是通过从头合成制备的。三聚体的形成依赖于基于溴封端和正交活化的低聚物统一方法，达到了报告的天然产物结构。

  DOI：

  10.1039/c2ob26337h

文献信息

• Synthesis of epigallocatechin trimer, (epigallocatechin)2-epicatechin, and (epigallocatechin)2-catechin via a Lewis acid mediated one-pot condensation and their antitumor activities in prostate cancer cells
  作者：Mikihiro Ichikawa、Shinya Yamamoto、Chisato Ishihara、Shuhei Nonobe、Yasunao Hattori、Koji Umezawa、Hiroshi Fujii、Hidefumi Makabe

  DOI：10.1016/j.tet.2018.04.089

  日期：2018.7

  Syntheses of epigallocatechin trimer, (epigallocatechin)(2)-epicatechin and (epigallocatechin)(2)-catechin were achieved. The key condensation to form the proanthocyanidin trimer derivatives was accomplished in a one-pot procedure using a dimeric epigallocatechin electrophile, which was prepared in situ by self-condensation of an epigallocatechin derivative, and an epigallocatechin, epicatechin, or catechin derivative as the nucleophile in the presence of a Lewis acid. The epigallocatechin monomer to trimer compounds containing a pyrogallol group significantly suppressed cell proliferation in PC-3 prostate cancer cells. (C) 2018 Elsevier Ltd. All rights reserved.
• Syntheses of prodelphinidin B1, B2, and B4 and their antitumor activities against human PC-3 prostate cancer cell lines
  作者：Wataru Fujii、Kazuya Toda、Kiriko Matsumoto、Koichiro Kawaguchi、Sei-ichi Kawahara、Yasunao Hattori、Hiroshi Fujii、Hidefumi Makabe

  DOI：10.1016/j.tetlet.2013.10.113

  日期：2013.12

  Total synthesis of prodelphinidin B1, B2, and B4 has been accomplished. The key step is Lewis acid-mediated equimolar condensations between an epigallocatechin and/or a gallocatechin nucleophile and an epigallocatechin and/or a gallocatechin electrophile. The antitumor effects of synthetic prodelphinidin B1-B4 against human PC-3 prostate cancer cell lines have been investigated. These compounds showed significant antitumor effects. Their activity seemed to be little bit stronger than EGCG and prodelphinidin B3, known antitumor agent. (C) 2013 Elsevier Ltd. All rights reserved.