(2R,3S,4S)-2-[3,4-bis(phenylmethoxy)phenyl]-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromene-3,4-diol | 137624-11-4

• 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)-2-[3,4-bis(phenylmethoxy)phenyl]-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromene-3,4-diol
• CAS: 137624-11-4
• 化学式: C₄₃H₃₈O₇
• 分子量: 666.771
• InChiKey: QBYDZRUSARFBQM-KWDKOVGYSA-N

物化性质

• 沸点：
  811.8±65.0 °C(Predicted)
• 密度：
  1.271±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  50
• 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：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S)-2-[3,4-bis(phenylmethoxy)phenyl]-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromene-3,4-diol 在 palladium on activated charcoal 三氟化硼乙醚 、 氢气 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 苯 为溶剂， 反应 8.5h， 生成 (2R,3S)-2-(3,4-Dihydroxy-phenyl)-4-(2,4,6-trihydroxy-phenyl)-chroman-3,5,7-triol
  参考文献：
  名称：

  Synthesis of high molecular mass condensed tannin by cationic polymerization of flavan 3,4-carbonate

  摘要：

  一种制备高分子质量（最高；10 200）缩合单宁的新合成方法已经开发出来。 3′,4′,5,7-四苄基黄烷-3,4-碳酸酯 2 的聚合和随后的脱苄基反应得到了高分子质量的缩合单宁。随着反应时间的延长，合成单宁的分子量会增加到聚合度（）35。这种首次合成的高分子量缩合单宁可作为高分子量天然缩合单宁的模型化合物，例如从日本柿子（Diospyros kaki L.）果实中提取的单宁。

  DOI：

  10.1039/a606783b
• 作为产物：
  描述：

  (2R,3S,4S)-2-[3,4-bis(phenylmethoxy)phenyl]-3-[tert-butyl(dimethyl)silyl]oxy-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-4-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以96%的产率得到(2R,3S,4S)-2-[3,4-bis(phenylmethoxy)phenyl]-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromene-3,4-diol
  参考文献：
  名称：

  Synthesis of procyanidins by stepwise- and self-condensation using 3,4-cis-4-acetoxy-3-O-acetyl-4-dehydro-5,7,3′,4′-tetra-O-benzyl-(+)-catechin and (−)-epicatechin as a key building monomer

  摘要：

  3,4-cis-4-Acetoxy-3-O-acetyl-4-dehydro-5,7,3',4'-tetra-O-benzyl-(+)-catechin (1a) or (-)-epicatechin (1b) reacted high regio- and stereo-selectively with 1.5 equiv of the 5,7,3',4'-tetra-O-benzyloxyflavan-3-ol (4a or 4b) in the presence of 1 equiv of TMSOTf to give the corresponding procyanidins. On the other hand, the self-condensation of la in the presence of a catalytic amount of B(C6F5)(3) afforded wide-range procyanidins from dimer to 15-mer like a biomass. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.02.173

文献信息

• Synthetic Studies of Proanthocyanidins. Highly Stereoselective Synthesis of the Catechin Dimer, Procyanidin-B3
  作者：Akiko SAITO、Noriyuki NAKAJIMA、Akira TANAKA、Makoto UBUKATA

  DOI：10.1271/bbb.66.1764

  日期：2002.1.1

  A stereoselective synthesis of benzylated procyanidin-B3, a condensed catechin dimer, is described. Condensation of 5,7,3′,4′-tetrabenzylcatechin with (2R,3S,4S)-5,7,3′,4′-tetrabenzyloxy-3-acetoxy-4-methoxyflavan as an electrophile in the presence of TiCl4 led to octabenzylated procyanidin-B3 stereoselectively.

  描述了苯甲基化原花青定-B3（一种缩合儿茶素二聚体）的手性合成。在TiCl4存在下，以5,7,3′,4′-四苯甲基儿茶素与(2R,3S,4S)-5,7,3′,4′-四苯甲氧基-3-乙酰氧基-4-甲氧基黄烷作为亲电试剂进行缩合反应，得到选择性的八苯甲基化原花青定-B3。
• Deuterium labeled procyanidin syntheses
  作者：Marie-Clotilde Pierre、Catherine Chèze、Joseph Vercauteren

  DOI：10.1016/s0040-4039(97)01269-0

  日期：1997.8

  Deuterium-labeled procyanidins have been prepared by hemisynthesis from taxifolin in order to investigate their metabolism in human. The structures of the desired deuterated natural compounds B3 10D (R-1=D, R-2=H) and B4 13D (R-1=D, R-2=H) were proven by spectroscopic and physical properties means, including H-2 NMR spectrum. By-products with unatural absolute configuration at some centers were also formed along the process and were characterised. (C) 1997 Elsevier Science Ltd.