(1R,3R,4R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexanecarbaldehyde | 906066-56-6

• 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: (1R,3R,4R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexanecarbaldehyde
• 英文别名: (1R,3R,4R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]cyclohexane-1-carbaldehyde
• CAS: 906066-56-6
• 化学式: C₁₉H₄₀O₃Si₂
• 分子量: 372.696
• InChiKey: XGCFSSPIOMAUCJ-BRWVUGGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.77
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 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：

  (1R,3R,4R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexanecarbaldehyde 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 7.0h， 生成 (4R,5S)-3-{3-[(1S,3R,4R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-propionyl}-4-methyl-5-phenyl-oxazolidin-2-one
  参考文献：
  名称：

  Studies directed towards the synthesis of antascomicin A: stereoselective synthesis of the C22–C34 fragment of the molecule

  摘要：

  A stereoselective synthesis of the C22-C34 fragment of the non-immunosuppressive immunophilin-binding natural product, antascomicin A was achieved using D-quinic acid as the starting material and highly stereoselective aldol reactions were employed, as key steps, to build the remaining stereocentres at C23, C26 and C27. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.05.115
• 作为产物：
  描述：

  methyl (1R,3R,4R)-4-benzoyloxy-3-hydroxycyclohexane-1-carboxylate 在 2,6-二甲基吡啶 、 2,4,6-三甲基吡啶 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.25h， 生成 (1R,3R,4R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexanecarbaldehyde
  参考文献：
  名称：

  Studies directed towards the synthesis of antascomicin A: stereoselective synthesis of the C22–C34 fragment of the molecule

  摘要：

  A stereoselective synthesis of the C22-C34 fragment of the non-immunosuppressive immunophilin-binding natural product, antascomicin A was achieved using D-quinic acid as the starting material and highly stereoselective aldol reactions were employed, as key steps, to build the remaining stereocentres at C23, C26 and C27. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.05.115