[(2R,3S,4S)-4-[(2R,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-3-hydroxy-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-8-yl]-5,7-bis(phenylmethoxy)-2-[3,4,5-tris(phenylmethoxy)phenyl]-3,4-dihydro-2H-chromen-3-yl] acetate | 1429125-64-3

• 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,3S,4S)-4-[(2R,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-3-hydroxy-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-8-yl]-5,7-bis(phenylmethoxy)-2-[3,4,5-tris(phenylmethoxy)phenyl]-3,4-dihydro-2H-chromen-3-yl] acetate
• CAS: 1429125-64-3
• 化学式: C₉₅H₈₂O₁₄
• 分子量: 1447.69
• InChiKey: NMDLBQQCBCSKLS-KIVBYONVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19
• 重原子数：
  109
• 可旋转键数：
  32
• 环数：
  15.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  148
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4S)-4-[(2R,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-3-hydroxy-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-8-yl]-5,7-bis(phenylmethoxy)-2-[3,4,5-tris(phenylmethoxy)phenyl]-3,4-dihydro-2H-chromen-3-yl] acetate 在 四丁基氢氧化铵 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以82%的产率得到(2R,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-8-[(2R,3S,4S)-3-hydroxy-5,7-bis(phenylmethoxy)-2-[3,4,5-tris(phenylmethoxy)phenyl]-3,4-dihydro-2H-chromen-4-yl]-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-3-ol
  参考文献：
  名称：

  Syntheses of prodelphinidin B3 and C2, and their antitumor activities through cell cycle arrest and caspase-3 activation

  摘要：

  Total synthesis of prodelphinidin B3 and C2 have been accomplished. The key step is Lewis acid-mediated equimolar condensations between a catechin and/or gallocatechin nucleophile and a gallocatechin electrophile. The antitumor effects of synthetic prodelphidin B3 and C2 against PC-3 prostate cancer cell lines have been investigated. Both compounds showed significant antitumor effects. Their activity was almost the same as that of EGCG, a known antitumor agent. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.02.087
• 作为产物：
  描述：

  (2R,3S,4S)-3-acetoxy-4-(2-ethoxyethoxy)-5,7,3',4',5'-pentabenzyloxyflavan 、 (2R,3S)-5,7-二(苄氧基)-2-[3,4-二(苄氧基)苯基]-3-色满醇 在 ytterbium(III) triflate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以86%的产率得到[(2R,3S,4S)-4-[(2R,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-3-hydroxy-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-8-yl]-5,7-bis(phenylmethoxy)-2-[3,4,5-tris(phenylmethoxy)phenyl]-3,4-dihydro-2H-chromen-3-yl] acetate
  参考文献：
  名称：

  Syntheses of prodelphinidin B3 and C2, and their antitumor activities through cell cycle arrest and caspase-3 activation

  摘要：

  Total synthesis of prodelphinidin B3 and C2 have been accomplished. The key step is Lewis acid-mediated equimolar condensations between a catechin and/or gallocatechin nucleophile and a gallocatechin electrophile. The antitumor effects of synthetic prodelphidin B3 and C2 against PC-3 prostate cancer cell lines have been investigated. Both compounds showed significant antitumor effects. Their activity was almost the same as that of EGCG, a known antitumor agent. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.02.087