(3S,4S)-4-methyl-4-phenyl-3-tris(trimethylsilyl)siloxybutanal | 875288-47-4

• 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: (3S,4S)-4-methyl-4-phenyl-3-tris(trimethylsilyl)siloxybutanal
• 英文别名: (3S,4S)-4-phenyl-3-tris(trimethylsilyl)silyloxypentanal
• CAS: 875288-47-4
• 化学式: C₂₀H₄₀O₂Si₄
• 分子量: 424.878
• InChiKey: WXSRSGJXUGKNOE-ICSRJNTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.96
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  (3S,4S)-4-methyl-4-phenyl-3-tris(trimethylsilyl)siloxybutanal 在 4-甲基苯磺酸吡啶 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 9.02h， 生成
  参考文献：
  名称：

  “Super Silyl” Group for Diastereoselective Sequential Reactions:  Access to Complex Chiral Architecture in One Pot

  摘要：

  We have shown that the tris(trimethylsilyl)silyl (TTMSS) silyl enol ether of acetaldehyde undergoes aldehyde cross-aldol reactions with high selectivity and the extremely low catalyst loading (0.05 mol % of HNTf2) allows for one-pot sequential reactions where acidic or basic nucleophiles can be subsequently added. Various ketone-derived silyl enol ethers, Grignard reagents, and dienes succeeded, generating relatively complex molecular architectures in a single step. This represents the first case where, in a single pot, highly acidic conditions followed by very basic conditions were tolerated to give products with high diastereoselectivities and good yields.

  DOI：

  10.1021/ja0693542
• 作为产物：
  描述：

  三(三甲基硅基)硅烷 在 三氟甲磺酸 、 双三氟甲烷磺酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.25h， 生成 (3S,4S)-4-methyl-4-phenyl-3-tris(trimethylsilyl)siloxybutanal
  参考文献：
  名称：

  Tris(trimethylsilyl)silyl-Governed Aldehyde Cross-Aldol Cascade Reaction

  摘要：

  The use of the tris(trimethylsilyl)silyl (TTMSS) group in aldehyde-derived silyl enol ethers affords aldehyde cross-aldol products with high yields and allows for unprecedented reactivity. The reaction is catalyzed by 0.05 mol % of HNTf2, and can easily be managed to give beta,delta-bis-, beta,delta,gamma-tris-, and beta,delta,zeta-tris-hydroxy-aldehydes with extremely high selectivity by simple stoichiometric control. High diastereoselectivity is obtained in all cases, and the use of chiral aldehydes affords Felkin products when there are nonchelating substituents, chelation products when there is a chelating sbustituent, and syn products when there is beta-substitution. HNTf2 is proposed to be an initiator, and highly Lewis acidic TTMSSNTf2 is the true catalyst.

  DOI：

  10.1021/ja054725k

文献信息

• “Super Silyl” Group for Diastereoselective Sequential Reactions:  Access to Complex Chiral Architecture in One Pot
  作者：Matthew B. Boxer、Hisashi Yamamoto

  DOI：10.1021/ja0693542

  日期：2007.3.1

  We have shown that the tris(trimethylsilyl)silyl (TTMSS) silyl enol ether of acetaldehyde undergoes aldehyde cross-aldol reactions with high selectivity and the extremely low catalyst loading (0.05 mol % of HNTf2) allows for one-pot sequential reactions where acidic or basic nucleophiles can be subsequently added. Various ketone-derived silyl enol ethers, Grignard reagents, and dienes succeeded, generating relatively complex molecular architectures in a single step. This represents the first case where, in a single pot, highly acidic conditions followed by very basic conditions were tolerated to give products with high diastereoselectivities and good yields.
• Tris(trimethylsilyl)silyl-Governed Aldehyde Cross-Aldol Cascade Reaction
  作者：Matthew B. Boxer、Hisashi Yamamoto

  DOI：10.1021/ja054725k

  日期：2006.1.1

  The use of the tris(trimethylsilyl)silyl (TTMSS) group in aldehyde-derived silyl enol ethers affords aldehyde cross-aldol products with high yields and allows for unprecedented reactivity. The reaction is catalyzed by 0.05 mol % of HNTf2, and can easily be managed to give beta,delta-bis-, beta,delta,gamma-tris-, and beta,delta,zeta-tris-hydroxy-aldehydes with extremely high selectivity by simple stoichiometric control. High diastereoselectivity is obtained in all cases, and the use of chiral aldehydes affords Felkin products when there are nonchelating substituents, chelation products when there is a chelating sbustituent, and syn products when there is beta-substitution. HNTf2 is proposed to be an initiator, and highly Lewis acidic TTMSSNTf2 is the true catalyst.