(4R,5R,8S,E)-5,9-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4,6,8-trimethylnon-6-en-3-one | 1004972-67-1

• 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: (4R,5R,8S,E)-5,9-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4,6,8-trimethylnon-6-en-3-one
• 英文别名: (E,4R,5R,8S)-5,9-bis[[tert-butyl(dimethyl)silyl]oxy]-4,6,8-trimethylnon-6-en-3-one
• CAS: 1004972-67-1
• 化学式: C₂₄H₅₀O₃Si₂
• 分子量: 442.83
• InChiKey: NDBRHCVIVFGXRH-PNBHLVAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  (4R,5R,8S,E)-5,9-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4,6,8-trimethylnon-6-en-3-one 、 三氟甲磺酸三甲基硅酯 在 lutidine 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到(2Z,4R,5R,6E,8S)-5,9-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4,6,8-trimethyl-3-(trimethylsilyloxy)-nona-2,6-diene
  参考文献：
  名称：

  Anti Aldol Selectivity in a Synthetic Approach to the C₁−C₁₂ Fragment of the Tedanolides

  摘要：

  In a synthetic approach to the completely protected C-1-C-12 fragment of the macrocyclic cytotoxic agent tedanolide 1, we carried out the tin-catalyzed Mukaiyama aldol reaction between the 2,3-dialkoxypropanal 5 and the silyl enol ether 6 derived from the ketone 7, which gave, unexpectedly, the anti aldol isomer, rather than the expected syn isomer 4, as the major diastereomer formed.

  DOI：

  10.1021/ol702729u
• 作为产物：
  描述：

  C₁₂H₂₂O₃ 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以470 mg的产率得到(4R,5R,8S,E)-5,9-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4,6,8-trimethylnon-6-en-3-one
  参考文献：
  名称：

  Anti Aldol Selectivity in a Synthetic Approach to the C₁−C₁₂ Fragment of the Tedanolides

  摘要：

  In a synthetic approach to the completely protected C-1-C-12 fragment of the macrocyclic cytotoxic agent tedanolide 1, we carried out the tin-catalyzed Mukaiyama aldol reaction between the 2,3-dialkoxypropanal 5 and the silyl enol ether 6 derived from the ketone 7, which gave, unexpectedly, the anti aldol isomer, rather than the expected syn isomer 4, as the major diastereomer formed.

  DOI：

  10.1021/ol702729u

文献信息

• Anti Aldol Selectivity in a Synthetic Approach to the C₁−C₁₂ Fragment of the Tedanolides
  作者：Michael E. Jung、Ting-hu Zhang

  DOI：10.1021/ol702729u

  日期：2008.1.1

  In a synthetic approach to the completely protected C-1-C-12 fragment of the macrocyclic cytotoxic agent tedanolide 1, we carried out the tin-catalyzed Mukaiyama aldol reaction between the 2,3-dialkoxypropanal 5 and the silyl enol ether 6 derived from the ketone 7, which gave, unexpectedly, the anti aldol isomer, rather than the expected syn isomer 4, as the major diastereomer formed.