(1'S,3R)-1-[(1-methoxy-2,2,2-triphenylethyl)dimethylsilyloxy]octan-3-ol | 952651-94-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (1'S,3R)-1-[(1-methoxy-2,2,2-triphenylethyl)dimethylsilyloxy]octan-3-ol
• 英文别名: (3R)-1-[[(1S)-1-methoxy-2,2,2-triphenylethyl]-dimethylsilyl]oxyoctan-3-ol
• CAS: 952651-94-4
• 化学式: C₃₁H₄₂O₃Si
• 分子量: 490.758
• InChiKey: VFNZCILJMSYULL-IHLOFXLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.13
• 重原子数：
  35
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  (1'S,3R)-1-[(1-methoxy-2,2,2-triphenylethyl)dimethylsilyloxy]octan-3-ol 在 lithium aluminium tetrahydride 、 溴 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 1.67h， 生成 (S)-1-{2-[(1-methoxy-2,2,2-triphenylethyl)dimethylsilyloxy]phenyl}ethanone
  参考文献：
  名称：

  More than a Protective Group:  Synthesis and Applications of a New Chiral Silane

  摘要：

  Enantiomerically pure (-)-(R)- and (+)-(S)-(1-methoxy-2,2,2-triphenylethyl)dimethylsilanes (MOTES-H) were synthesized from triphenylacetaidehyde in five synthetic steps and with 60% overall yield. MOTES-protected alpha- and beta-hydroxycarbonyl compounds were used in Grignard and Diels-Alder reactions in the presence of MgBr2 to afford addition products with 87-98% yield and selectivities of up to >120:1 dr. With this method, the pine beetle pheromone (-)-frontalin (67%, 98.5% ee) and naturally occurring (-)-(R)-octane-1,3-diol (90%, >99% ee) were synthesized.

  DOI：

  10.1021/ol071382h
• 作为产物：
  描述：

  (1'S)-[(1-methoxy-2,2,2-triphenylethyl)dimethylsilyloxy]propionaldehyde 、 正戊基溴化镁 在 magnesium bromide 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 0.33h， 生成 (1'S,3R)-1-[(1-methoxy-2,2,2-triphenylethyl)dimethylsilyloxy]octan-3-ol 、 (1'S,3S)-1-[(1-methoxy-2,2,2-triphenylethyl)dimethylsilyloxy]octan-3-ol
  参考文献：
  名称：

  More than a Protective Group:  Synthesis and Applications of a New Chiral Silane

  摘要：

  Enantiomerically pure (-)-(R)- and (+)-(S)-(1-methoxy-2,2,2-triphenylethyl)dimethylsilanes (MOTES-H) were synthesized from triphenylacetaidehyde in five synthetic steps and with 60% overall yield. MOTES-protected alpha- and beta-hydroxycarbonyl compounds were used in Grignard and Diels-Alder reactions in the presence of MgBr2 to afford addition products with 87-98% yield and selectivities of up to >120:1 dr. With this method, the pine beetle pheromone (-)-frontalin (67%, 98.5% ee) and naturally occurring (-)-(R)-octane-1,3-diol (90%, >99% ee) were synthesized.

  DOI：

  10.1021/ol071382h

文献信息

• More than a Protective Group:  Synthesis and Applications of a New Chiral Silane
  作者：Maurizio Campagna、Michael Trzoss、Stefan Bienz

  DOI：10.1021/ol071382h

  日期：2007.9.1

  Enantiomerically pure (-)-(R)- and (+)-(S)-(1-methoxy-2,2,2-triphenylethyl)dimethylsilanes (MOTES-H) were synthesized from triphenylacetaidehyde in five synthetic steps and with 60% overall yield. MOTES-protected alpha- and beta-hydroxycarbonyl compounds were used in Grignard and Diels-Alder reactions in the presence of MgBr2 to afford addition products with 87-98% yield and selectivities of up to >120:1 dr. With this method, the pine beetle pheromone (-)-frontalin (67%, 98.5% ee) and naturally occurring (-)-(R)-octane-1,3-diol (90%, >99% ee) were synthesized.