(1S,2S,3R,4R)-1-(tert-butyldimethylsilyloxy)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-methylhexane-2,4-diol | 1153605-43-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,3R,4R)-1-(tert-butyldimethylsilyloxy)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-methylhexane-2,4-diol
• 英文别名: (1S,2S,3R,4R)-1-[tert-butyl(dimethyl)silyl]oxy-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylhexane-2,4-diol
• CAS: 1153605-43-6
• 化学式: C₁₈H₃₈O₅Si
• 分子量: 362.582
• InChiKey: QAOJQZAJWFJFIH-RBGFHDKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2S,3R,4R)-1-(tert-butyldimethylsilyloxy)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-methylhexane-2,4-diol 、 2,2-二甲氧基丙烷 生成 tert-butyl-((S)-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)((4S,5R,3R,6R)-6-ethyl-2,2,5-trimethyl-1,3-dioxan-4-yl)methoxy)dimethylsilane
  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
• 作为产物：
  描述：

  (4S,5S,6S)-6-(tert-butyldimethylsilyloxy)-6-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-5-hydroxy-4-methylhexan-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61%的产率得到(1S,2S,3R,4R)-1-(tert-butyldimethylsilyloxy)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-methylhexane-2,4-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