(2R,3S)-2-(4-benzyloxyphenyl)-7-benzyloxychroman-3-ol | 850816-16-9

• 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)-2-(4-benzyloxyphenyl)-7-benzyloxychroman-3-ol
• 英文别名: 2,3-trans-7,4'-bis(benzyloxy)flavan-3-ol；(2R,3S)-7-phenylmethoxy-2-(4-phenylmethoxyphenyl)-3,4-dihydro-2H-chromen-3-ol
• CAS: 850816-16-9
• 化学式: C₂₉H₂₆O₄
• 分子量: 438.523
• InChiKey: PFHBFXITNKQIEZ-LMSSTIIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2-(4-benzyloxyphenyl)-7-benzyloxychroman-3-ol 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 、 5%-palladium/activated carbon 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 3.42h， 生成 雌马酚
  参考文献：
  名称：

  黄烷-异黄烷重排：通过1,2-移位-烷基化序列进行生物启发的异黄酮类合成途径。

  摘要：

  据报道，基于儿茶素骨架中芳基的1,2-转移，然后进行原位烷基化，可以实现2-取代异黄酮的制备。合成了具有雌激素活性的天然异黄酮（-）-雌马酚。

  DOI：

  10.1039/c5cc01572c
• 作为产物：
  描述：

  (E)-1-(4-(benzyloxy)-2-hydroxyphenyl)-3-(4-(benzyloxy)phenyl)prop-2-en-1-one 在 咪唑 、 AD-mix-α 、 甲基磺酰胺 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 氯甲酸乙酯 、 potassium carbonate 、 三乙胺 、 原甲酸三乙酯 作用下， 以 四氢呋喃 、 甲醇 、 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 7.5h， 生成 (2R,3S)-2-(4-benzyloxyphenyl)-7-benzyloxychroman-3-ol
  参考文献：
  名称：

  (+)-Myristinin A, a Naturally Occurring DNA Polymerase β Inhibitor and Potent DNA-Damaging Agent

  摘要：

  The first stereoselective total synthesis of the naturally occurring flavan myristinin A has been accomplished, as well as its biochemical evaluation. This synthesis verified the structural assignment and allowed for the determination of the absolute stereochemistry. Myristinin A exhibits biochemical activity both as a potent DNA-damaging agent and DNA polymerase beta inhibitor. Relaxation of supercoiled plasmid DNA was observed at picomolar concentrations, in addition to inhibition of polymerase beta at low micromolar concentrations.

  DOI：

  10.1021/ja042727j

文献信息

• Enantioselective Synthesis of Flavan-3-ols Using a Mitsunobu Cyclization
  作者：Karsten Krohn、Ishtiaq Ahmed、Markus John

  DOI：10.1055/s-0028-1083361

  日期：——

  The synthesis of four flavan-3-ols with different substitution patterns and electron densities has been achieved in high stereo- and regioselectivity by a one-step Mitsunobu reaction from the corresponding diols, which were prepared by enantioselective Sharpless dihydroxylation of suitable olefins. The six-membered flavan-3-ols were the only cyclization products and the theoretically possible formation of five-membered rings during the Mitsunobu cyclization was not observed. The flavanols are important starting materials for the synthesis of dimers such as the procyanidins or other coupling products such as the flavan part of the potent DNA polymerase β inhibitor myristinin A. The enantioselectivities of both the Sharpless dihydroxylation and the Mitsunobu cyclization steps were monitored by chiral HPLC.

  通过从相应的二醇进行一步Mitsunobu反应，以高立体选择性和区位选择性成功合成了四种具有不同取代模式和电子密度的黄酮-3-醇，这些二醇是通过对合适的烯烃进行手性选择性的Sharpless二羟基化制备的。在Mitsunobu环化过程中，六元环的黄酮-3-醇是唯一的环化产物，理论上可能形成的五元环并未被观察到。这些黄酮醇是合成二聚体（如原花青素）或其他偶联产物（如强效DNA聚合酶β抑制剂myristinin A中的黄酮部分）的重要起始材料。Sharpless二羟基化和Mitsunobu环化步骤的对映选择性通过手性高效液相色谱法进行了监测。
• Stereoselective Synthesis of the Atropisomers of Myristinin B/C
  作者：David J. Maloney、Shengxi Chen、Sidney M. Hecht

  DOI：10.1021/ol060511b

  日期：2006.4.1

  [reaction: see text] The first stereoselective synthesis of a potent DNA damaging agent, (-)-myristinin B/C, has been accomplished. This efficient synthesis allowed for unambiguous confirmation of the structure and absolute stereochemistry of the atropisomeric natural product. The antipode, (+)-myristinin B/C, was also synthesized, providing ample material for biological evaluation of both enantiomers

  [反应：见正文]已经完成了一种有效的DNA破坏剂（-）-myristinin B / C的首次立体选择性合成。这种有效的合成可以明确确认阻转异构天然产物的结构和绝对立体化学。还合成了对映体（+）-肉豆蔻素B / C，为两种对映体的生物学评估提供了充足的材料。
• The flavan–isoflavan rearrangement: bioinspired synthetic access to isoflavonoids via 1,2-shift–alkylation sequence
  作者：Kayo Nakamura、Ken Ohmori、Keisuke Suzuki

  DOI：10.1039/c5cc01572c

  日期：——

  An approach to 2-substituted isoflavonoids is reported based on the 1,2-shift of the aryl group in the catechin skeleton followed by the in situ alkylation. Synthesis of (-)-equol, a natural isoflavan with estrogenic activities, was achieved.

  据报道，基于儿茶素骨架中芳基的1,2-转移，然后进行原位烷基化，可以实现2-取代异黄酮的制备。合成了具有雌激素活性的天然异黄酮（-）-雌马酚。
• (+)-Myristinin A, a Naturally Occurring DNA Polymerase β Inhibitor and Potent DNA-Damaging Agent
  作者：David J. Maloney、Jing-Zhen Deng、Shelley R. Starck、Zhijie Gao、Sidney M. Hecht

  DOI：10.1021/ja042727j

  日期：2005.3.1

  The first stereoselective total synthesis of the naturally occurring flavan myristinin A has been accomplished, as well as its biochemical evaluation. This synthesis verified the structural assignment and allowed for the determination of the absolute stereochemistry. Myristinin A exhibits biochemical activity both as a potent DNA-damaging agent and DNA polymerase beta inhibitor. Relaxation of supercoiled plasmid DNA was observed at picomolar concentrations, in addition to inhibition of polymerase beta at low micromolar concentrations.