(2S,3S)-2-methyl-3-phenyl-3-(trimethylsilyloxy)propanal | 409360-80-1

• 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: (2S,3S)-2-methyl-3-phenyl-3-(trimethylsilyloxy)propanal
• 英文别名: (2S,3S)-2-methyl-3-phenyl-3-trimethylsilyloxypropanal
• CAS: 409360-80-1
• 化学式: C₁₃H₂₀O₂Si
• 分子量: 236.386
• InChiKey: SNMQNQOZSCLTEE-YPMHNXCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1E)-1-ethoxy-1-(trimethylsiloxy)propene 、 (2S,3S)-2-methyl-3-phenyl-3-(trimethylsilyloxy)propanal 在 (S)-4-Isopropyl-3-tosyl-[1,3,2]oxazaborolidin-5-one 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 ethyl (2S,3R,4R,5S)-3-hydroxy-2,4-dimethyl-5-phenyl-5-(trimethylsilyloxy)pentanoate 、 ethyl (2R,3R,4R,5S)-3-hydroxy-2,4-dimethyl-5-phenyl-5-(trimethylsilyloxy)pentanoate
  参考文献：
  名称：

  Superior substrate control on diastereoselection in boric Lewis acid-promoted aldol reactions. Asymmetric synthesis of a 3,4-syn homologous series of ethyl 3,5-dihydroxy-2,4-dimethyl-5-phenylpentanoates

  摘要：

  The BF3. OEt2-promoted aldol reaction of chiral syn- and anti-alpha -methyl-beta -siloxy aldehydes with a silyl ketene acetal resulted in essentially complete syn Felkin selection. Even in the asymmetric aldol reaction using chiral oxazaborolidinones, the substrate control with respect to diastereoselection was found to overcome the promoter (catalyst) control which would normally occur depending on the stereocenter of the chiral boranes. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00405-0
• 作为产物：
  描述：

  ethyl (2S,3S)-3-hydroxy-2-methyl-3-phenylpropanoate 在 2,6-二甲基吡啶 、 草酰氯 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.5h， 生成 (2S,3S)-2-methyl-3-phenyl-3-(trimethylsilyloxy)propanal
  参考文献：
  名称：

  Superior substrate control on diastereoselection in boric Lewis acid-promoted aldol reactions. Asymmetric synthesis of a 3,4-syn homologous series of ethyl 3,5-dihydroxy-2,4-dimethyl-5-phenylpentanoates

  摘要：

  The BF3. OEt2-promoted aldol reaction of chiral syn- and anti-alpha -methyl-beta -siloxy aldehydes with a silyl ketene acetal resulted in essentially complete syn Felkin selection. Even in the asymmetric aldol reaction using chiral oxazaborolidinones, the substrate control with respect to diastereoselection was found to overcome the promoter (catalyst) control which would normally occur depending on the stereocenter of the chiral boranes. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00405-0

文献信息

• Superior substrate control on diastereoselection in boric Lewis acid-promoted aldol reactions. Asymmetric synthesis of a 3,4-syn homologous series of ethyl 3,5-dihydroxy-2,4-dimethyl-5-phenylpentanoates
  作者：Syun-ichi Kiyooka、Kazi A. Shahid、Kazunori Murai、Yong-Nan Li、Momotoshi Okazaki、Yoshihiro Shuto

  DOI：10.1016/s0957-4166(01)00405-0

  日期：2001.9

  The BF3. OEt2-promoted aldol reaction of chiral syn- and anti-alpha -methyl-beta -siloxy aldehydes with a silyl ketene acetal resulted in essentially complete syn Felkin selection. Even in the asymmetric aldol reaction using chiral oxazaborolidinones, the substrate control with respect to diastereoselection was found to overcome the promoter (catalyst) control which would normally occur depending on the stereocenter of the chiral boranes. (C) 2001 Elsevier Science Ltd. All rights reserved.