(2S,5S,6R)-6-(hydroxymethyl)-2-(4-methoxyphenyl)-5,6-dihydro-2H-pyran-5-ol | 1011254-16-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2S,5S,6R)-6-(hydroxymethyl)-2-(4-methoxyphenyl)-5,6-dihydro-2H-pyran-5-ol
• 英文别名: (2R,3S,6S)-2-(hydroxymethyl)-6-(4-methoxyphenyl)-3,6-dihydro-2H-pyran-3-ol
• CAS: 1011254-16-2
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: VVVIKEZAGBOJEL-RWMBFGLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,5S,6R)-6-(hydroxymethyl)-2-(4-methoxyphenyl)-5,6-dihydro-2H-pyran-5-ol 在 三乙基硅烷 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以85%的产率得到
  参考文献：
  名称：

  Titanium tetrachloride mediated reductive ring opening of C-aryl pseudoglycals

  摘要：

  A facile reductive ring opening of C-aryl pseudoglycals is reported for the first time. The combination of titanium tetrachloride (Lewis acid) and triethylsilane (reducing agent) at -78 degrees C in dichloromethane is a mild and efficient reagent system for this transformation. The reagent system was successfully tested on various C-aryl pseudoglycal substrates to yield the corresponding ring opened products containing two asymmetric hydroxyls and a cis-double bond. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.175
• 作为产物：
  描述：

  1'-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-4'-methoxybenzene 在 甲醇 、 potassium carbonate 作用下， 反应 2.0h， 以96%的产率得到(2S,5S,6R)-6-(hydroxymethyl)-2-(4-methoxyphenyl)-5,6-dihydro-2H-pyran-5-ol
  参考文献：
  名称：

  Asymmetric Synthesis of (-)-6-epi-Centrolobine

  摘要：

  本研究首次描述了一种立体选择性全合成方法，即从容易获得的三-O-乙酰基-d-葡萄糖醛开始，合成 (-)-6-epi-centrobine 这种 (-)-centrobine 的非天然类似物。该合成方法的关键步骤是立体选择性 C-糖苷化、脱羟基和 Wittig 反应。通过九个步骤就得到了目标分子，总收率为 49%。

  DOI：

  10.1055/s-2008-1067218

文献信息

• Titanium tetrachloride mediated reductive ring opening of C-aryl pseudoglycals
  作者：Ch. Raji Reddy、G. Balakrishna Reddy、Ch. Lohitha Rao

  DOI：10.1016/j.tetlet.2007.11.175

  日期：2008.1

  A facile reductive ring opening of C-aryl pseudoglycals is reported for the first time. The combination of titanium tetrachloride (Lewis acid) and triethylsilane (reducing agent) at -78 degrees C in dichloromethane is a mild and efficient reagent system for this transformation. The reagent system was successfully tested on various C-aryl pseudoglycal substrates to yield the corresponding ring opened products containing two asymmetric hydroxyls and a cis-double bond. (C) 2007 Elsevier Ltd. All rights reserved.
• Asymmetric Synthesis of (-)-6<i>-epi</i>-Centrolobine
  作者：Chada Reddy、Pasupulety Madhavi、Srivari Chandrasekhar

  DOI：10.1055/s-2008-1067218

  日期：2008.9

  A stereoselective total synthesis of (-)-6-epi-centro­lobine, an unnatural analogue of (-)-centrolobine, starting from readily available tri-O-acetyl-d-glucal has been described for the first time. The key steps involved in this synthetic approach are stereoselective C-glycosidation, dehydroxylation and Wittig reaction. The target molecule was achieved in nine steps with 49% overall yield.

  本研究首次描述了一种立体选择性全合成方法，即从容易获得的三-O-乙酰基-d-葡萄糖醛开始，合成 (-)-6-epi-centrobine 这种 (-)-centrobine 的非天然类似物。该合成方法的关键步骤是立体选择性 C-糖苷化、脱羟基和 Wittig 反应。通过九个步骤就得到了目标分子，总收率为 49%。