(S)-3-(triisopropylsiloxy)butanal | 138835-75-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (S)-3-(triisopropylsiloxy)butanal
• 英文别名: (3S)-3-tri(propan-2-yl)silyloxybutanal
• CAS: 138835-75-3
• 化学式: C₁₃H₂₈O₂Si
• 分子量: 244.45
• InChiKey: BOUXQOKPRDSRPB-ZDUSSCGKSA-N

物化性质

• 沸点：
  264.9±23.0 °C(Predicted)
• 密度：
  0.860±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  (S)-3-(triisopropylsiloxy)butanal 在 palladium on activated charcoal 氢气 作用下， 生成 Hexanoic acid, 5-[[tris(1-methylethyl)silyl]oxy]-, methyl ester, (R)-
  参考文献：
  名称：

  Rychnovsky, Scott D.; Skalitzky, Donald J.; Pathirana, Charles, Journal of the American Chemical Society, 1992, vol. 114, # 2, p. 671 - 677

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl-(S)-3-(triisopropylsilyloxy)butyrate 在 二异丁基氢化铝 作用下， 生成 (S)-3-(triisopropylsiloxy)butanal
  参考文献：
  名称：

  Rychnovsky, Scott D.; Skalitzky, Donald J.; Pathirana, Charles, Journal of the American Chemical Society, 1992, vol. 114, # 2, p. 671 - 677

  摘要：

  DOI：

文献信息

• Stereodivergent Approach to the Avermectins Based on “Super Silyl” Directed Aldol Reactions
  作者：Patrick B. Brady、Susumu Oda、Hisashi Yamamoto

  DOI：10.1021/ol501327g

  日期：2014.8.1

  A stereodivergent approach to the spiroketal fragment of the avermectins is described. The strategy utilizes a sequence of three aldol reactions directed by the tris(trimethylsilyl)silyl “super silyl” group. Central to this strategy is that each aldol reaction can be controlled to allow access to either diastereomer in high stereoselectivity, thereby affording 16 stereoisomers along the same linear

  描述了阿维菌素的 spiroketal 片段的立体发散方法。该策略利用由三（三甲基甲硅烷基）甲硅烷基“超级甲硅烷基”基团引导的一系列三个羟醛反应。该策略的核心是可以控制每个羟醛反应以允许以高立体选择性获得任一非对映异构体，从而沿相同的线性骨架提供 16 个立体异构体。羟醛产物可以转化为螺酮，包括阿维菌素 A1a 全合成的高级中间体。
• 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.
• Rychnovsky, Scott D.; Skalitzky, Donald J.; Pathirana, Charles, Journal of the American Chemical Society, 1992, vol. 114, # 2, p. 671 - 677
  作者：Rychnovsky, Scott D.、Skalitzky, Donald J.、Pathirana, Charles、Jensen, Paul R.、Fenical, William

  DOI：——

  日期：——