(S)-3-((tert-butyldimethylsilyl)oxy)-4-((tert-butyldiphenylsilyl)oxy)butanal | 157758-30-0

• 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-((tert-butyldimethylsilyl)oxy)-4-((tert-butyldiphenylsilyl)oxy)butanal
• 英文别名: (S)-3-(tert-butyldimethylsilyloxy)-4-(tert-butyldiphenylsilyloxy) butanal；(3S)-3-[tert-butyl(dimethyl)silyl]oxy-4-[tert-butyl(diphenyl)silyl]oxybutanal
• CAS: 157758-30-0
• 化学式: C₂₆H₄₀O₃Si₂
• 分子量: 456.773
• InChiKey: IZTWMPFBKFRLQB-QFIPXVFZSA-N

物化性质

• 沸点：
  474.1±45.0 °C(predicted)
• 密度：
  0.99±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.54
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-((tert-butyldimethylsilyl)oxy)-4-((tert-butyldiphenylsilyl)oxy)butanal 在 正丁基锂 、 4-甲基苯磺酸吡啶 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 19.92h， 生成 6-(6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxan-4-yl)hex-5-yn-1-ol
  参考文献：
  名称：

  Controlling Regiochemistry in the Gold-Catalyzed Synthesis of Unsaturated Spiroketals

  摘要：

  A novel gold-catalyzed synthesis of unsaturated spiroketals that addresses regioselectivity issues commonly reported in metal-catalyzed spiroketalization of alkynes is reported. The reaction sequence is regulated by an acetonide protecting group which undergoes extrusion of acetone to deliver the desired spiroketals in good yields and diastereoselectivities. The reaction, which is carried out under very mild conditions employing AuCl as the catalyst, should be widely applicable in the synthesis of a broad range of spiroketals.

  DOI：

  10.1021/ol5024954
• 作为产物：
  描述：

  (S)-methyl 4-(tert-butyldiphenylsilyloxy)-3-hydroxybutanoate 在 2,6-二甲基吡啶 、 甲醇 、 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 (S)-3-((tert-butyldimethylsilyl)oxy)-4-((tert-butyldiphenylsilyl)oxy)butanal
  参考文献：
  名称：

  swinholide A的收敛方法。swinholideA C 3 –C 17片段的立体选择性构建

  摘要：

  一种用于细胞毒性二聚大环内酯swinholide A的总合成策略（1，方案1）中概述和的适当官能℃的立体结构3 -C 17片段4，开始与积木6，7，9和10中描述。

  DOI：

  10.1039/c39940001147

文献信息

• Divergent Approach to Building a Latrunculin Family Derived Hybrid Macrocyclic Toolbox
  作者：Madhu Aeluri、Bhanudas Dasari、Prabhat Arya

  DOI：10.1021/ol503465p

  日期：2015.2.6

  A divergent approach to obtain a latrunculin family based hybrid macrocyclic toolbox is developed. A practical, stereoselective synthesis of a common substructure present in latrunculin A and latrunculol A was achieved. This was further utilized in the macrocyclic diversity synthesis. The amino acid moiety embedded in the 15-membered macrocyclic ring allows for the exploration of various chiral side

  开发了一种获得基于拉特朗库林家族的混合大环工具箱的方法。实用，立体选择性地合成了latrunculin A和latrunculol A中存在的常见亚结构。这在大环分集合成中得到了进一步利用。嵌入15元大环的氨基酸部分允许探索各种手性侧链，作为多样性位点之一。
• Au-Catalyzed Cyclization of Monopropargylic Triols: An Expedient Synthesis of Monounsaturated Spiroketals
  作者：Aaron Aponick、Chuan-Ying Li、Jean A. Palmes

  DOI：10.1021/ol802491m

  日期：2009.1.1

  The gold-catalyzed cyclization of monopropargylic triols to form olefin-containing spiroketals is reported. The reactions are rapid and high yielding when 2 mol % of the catalyst generated in situ from Au[P(t-BU)(2)(o-biphenyI)]Cl and AgOTf is employed in THF at 0 degrees C. A range of differentially substituted triols leading to substituted 5- and 6-membered ring spiroketals were prepared and function well in the reaction.
• A convergent approach to swinholide A. Stereoselective construction of the C₃–C₁₇fragment of swinholide A
  作者：A. P. Patron、P. K. Richter、M. J. Tomaszewski、R. A. Miller、K. C. Nicolaou

  DOI：10.1039/c39940001147

  日期：——

  A strategy for a total synthesis of the cytotoxic dimeric macrolide swinholide A (1, Scheme 1) is outlined and a stereoselective construction of the suitably functionalized C3–C17 fragment 4, starting with building blocks 6, 7, 9 and 10 is described.

  一种用于细胞毒性二聚大环内酯swinholide A的总合成策略（1，方案1）中概述和的适当官能℃的立体结构3 -C 17片段4，开始与积木6，7，9和10中描述。
• Controlling Regiochemistry in the Gold-Catalyzed Synthesis of Unsaturated Spiroketals
  作者：Paulo H. S. Paioti、John M. Ketcham、Aaron Aponick

  DOI：10.1021/ol5024954

  日期：2014.10.17

  A novel gold-catalyzed synthesis of unsaturated spiroketals that addresses regioselectivity issues commonly reported in metal-catalyzed spiroketalization of alkynes is reported. The reaction sequence is regulated by an acetonide protecting group which undergoes extrusion of acetone to deliver the desired spiroketals in good yields and diastereoselectivities. The reaction, which is carried out under very mild conditions employing AuCl as the catalyst, should be widely applicable in the synthesis of a broad range of spiroketals.