(4R,5R,6S)-6-(tert-butyldimethylsilanyloxy)-5-hydroxy-4-methylheptan-3-one | 1153605-31-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R,6S)-6-(tert-butyldimethylsilanyloxy)-5-hydroxy-4-methylheptan-3-one
• CAS: 1153605-31-2
• 化学式: C₁₄H₃₀O₃Si
• 分子量: 274.476
• InChiKey: QIVSNCJJOSNLNP-GMXVVIOVSA-N

物化性质

• 沸点：
  330.9±32.0 °C(predicted)
• 密度：
  0.922±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  (4R,5R,6S)-6-(tert-butyldimethylsilanyloxy)-5-hydroxy-4-methylheptan-3-one 在 titanium(IV) tetrabutoxide 、 异丁醛 、 sodium methylate 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 以65%的产率得到(2S,3R,4S,5S)-2-(tert-butyldimethylsilyloxy)-4-methylheptane-3,5-diol
  参考文献：
  名称：

  Toward Asymmetric Aldol-Tishchenko Reactions with Enolizable Aldehydes: Access to Defined Configured Stereotriads, Tetrads, and Stereopentads

  摘要：

  Asymmetric aldol-Tishchenko, reactions of enolizable aldehydes and ketones in the presence of chiral BINOLTi(OtBU)(2)/Cinchona alkaloids complexes are described. Different configurative outcomes of these reactions depend on an equilibration through a retro aldol/aldol sequence and can be influenced by the configurative architecture of substrates. The results are explained by means of transition state models and rate constants. These considerations offer a fine-tuning of diastereoselectivity in aldol-Tishchenko reactions. Extensions of this research give access to defined configured stereotriads, stereotetrads, and stereopentads.

  DOI：

  10.1021/jo9003635