[(2R,6S)-6-(2-Benzyloxy-ethyl)-tetrahydro-pyran-2-yl]-methanol | 147332-41-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(2R,6S)-6-(2-Benzyloxy-ethyl)-tetrahydro-pyran-2-yl]-methanol
• 英文别名: [(2R,6S)-6-(2-phenylmethoxyethyl)oxan-2-yl]methanol
• CAS: 147332-41-0
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: POWLQYJLUZOQRX-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(2R,6S)-6-(2-Benzyloxy-ethyl)-tetrahydro-pyran-2-yl]-methanol 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 2-[(2S,6S)-(6-methyltetrahydropyran-2-yl)]ethanol
  参考文献：
  名称：

  A highly stereoselective synthetic method for cis-2- hydroxymethyl-6-alkyltetrahydropyrans

  摘要：

  A highly stereoselective synthetic method for cis-2-hydroxymethyl 6-alkyltetrahydropyrans is described by an intramolecular 1,4-addition of alcohol to alpha,beta-unsaturated sulfoxide as a key reaction. This method is applied to syntheses of (+) and (-)-(cis-6-methyltetrahydropyran-2-yl)acetic acid.

  DOI：

  10.1016/s0040-4039(00)60070-9
• 作为产物：
  描述：

  (2S,6R)-2-(2-Benzyloxy-ethyl)-6-((R)-toluene-4-sulfinylmethyl)-tetrahydro-pyran 在 lithium aluminium tetrahydride 、 sodium acetate 、 乙酸酐 作用下， 生成 [(2R,6S)-6-(2-Benzyloxy-ethyl)-tetrahydro-pyran-2-yl]-methanol
  参考文献：
  名称：

  A highly stereoselective synthetic method for cis-2- hydroxymethyl-6-alkyltetrahydropyrans

  摘要：

  A highly stereoselective synthetic method for cis-2-hydroxymethyl 6-alkyltetrahydropyrans is described by an intramolecular 1,4-addition of alcohol to alpha,beta-unsaturated sulfoxide as a key reaction. This method is applied to syntheses of (+) and (-)-(cis-6-methyltetrahydropyran-2-yl)acetic acid.

  DOI：

  10.1016/s0040-4039(00)60070-9

文献信息

• Stereoselective Reduction of Bicyclic Ketals. An Efficient Synthesis of (−)-(<i>R</i>,<i>R</i>)-(<i>cis</i>-6-Methyltetrahydropyran-2-yl)acetic Acid, an Enantiomer of Civet Cat Constituent
  作者：Hiyoshizo Kotsuki、Yasuyuki Ushio、Isao Kadota、Masamitsu Ochi

  DOI：10.1246/cl.1988.927

  日期：1988.6.5

  (−)-(R,R)-(cis-6-Methyltetrahydropyran-2-yl)acetic acid, an enantiomer of civet cat constituent, was prepared in high yield by using a stereoselective reduction of bicyclic ketals as a key step.

  (-)-(R,R)-(cis-6-Methyltetrahydropyran-2-yl)乙酸，麝猫猫成分的对映体，通过使用双环缩酮的立体选择性还原作为关键步骤以高产率制备。
• A highly stereoselective synthetic method for cis-2- hydroxymethyl-6-alkyltetrahydropyrans
  作者：Tadakatsu Mandai、Masayuki Ueda、Kaori Kashiwagi、Mikio Kawada、Jiro Tsuji

  DOI：10.1016/s0040-4039(00)60070-9

  日期：1993.1

  A highly stereoselective synthetic method for cis-2-hydroxymethyl 6-alkyltetrahydropyrans is described by an intramolecular 1,4-addition of alcohol to alpha,beta-unsaturated sulfoxide as a key reaction. This method is applied to syntheses of (+) and (-)-(cis-6-methyltetrahydropyran-2-yl)acetic acid.