(2S,3S,4R,6R,7R,10S,E)-3-hydroxy-7,11-bis[(1,1-dimethylethyl)dimethylsilyloxy]-1-[(1,1-dimethylethyl)diphenylsilyloxy]-4,6,8,10-tetramethyl-2-(phenylmethoxy)undec-8-en-5-one | 1004973-00-5

• 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: (2S,3S,4R,6R,7R,10S,E)-3-hydroxy-7,11-bis[(1,1-dimethylethyl)dimethylsilyloxy]-1-[(1,1-dimethylethyl)diphenylsilyloxy]-4,6,8,10-tetramethyl-2-(phenylmethoxy)undec-8-en-5-one
• 英文别名: (E,2S,3S,4R,6R,7R,10S)-7,11-bis[[tert-butyl(dimethyl)silyl]oxy]-1-[tert-butyl(diphenyl)silyl]oxy-3-hydroxy-4,6,8,10-tetramethyl-2-phenylmethoxyundec-8-en-5-one
• CAS: 1004973-00-5
• 化学式: C₅₀H₈₀O₆Si₃
• 分子量: 861.438
• InChiKey: KGBHQPXHORZGMV-JMDQTTGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.35
• 重原子数：
  59
• 可旋转键数：
  23
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,6R,7R,10S,E)-3-hydroxy-7,11-bis[(1,1-dimethylethyl)dimethylsilyloxy]-1-[(1,1-dimethylethyl)diphenylsilyloxy]-4,6,8,10-tetramethyl-2-(phenylmethoxy)undec-8-en-5-one 在 二异丁基氢化铝 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成
  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：

  (S)-3-[(1,1-dimethylethyl)diphenylsilyloxy]-2-(phenylmethoxy)propanal 、 (2Z,4R,5R,6E,8S)-5,9-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4,6,8-trimethyl-3-(trimethylsilyloxy)-nona-2,6-diene 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到(2S,3S,4R,6R,7R,10S,E)-3-hydroxy-7,11-bis[(1,1-dimethylethyl)dimethylsilyloxy]-1-[(1,1-dimethylethyl)diphenylsilyloxy]-4,6,8,10-tetramethyl-2-(phenylmethoxy)undec-8-en-5-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.