(E)-(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxy)-1,1-diethoxy-hex-3-en-2-ol | 158782-82-2

• 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: (E)-(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxy)-1,1-diethoxy-hex-3-en-2-ol
• 英文别名: (E,2R,5S)-5-[tert-butyl(diphenyl)silyl]oxy-1,1-diethoxyhex-3-en-2-ol
• CAS: 158782-82-2
• 化学式: C₂₆H₃₈O₄Si
• 分子量: 442.671
• InChiKey: CDKLRNRYCBEOEK-CEHCZICOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxy)-1,1-diethoxy-hex-3-en-2-ol 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 (2R,5S)-5-(tert-Butyl-diphenyl-silanyloxy)-1,1-diethoxy-hexan-2-ol
  参考文献：
  名称：

  Enantioselective Total Synthesis of the (−)-(6R,11R,14S)-Isomer of Colletallol

  摘要：

  The total synthesis of the (-)-(6R,11R,14S)-isomer of colletallol was achieved in 15 steps. The key steps of the sequence were the building of the macrocycle via two consecutive Wittig reactions, the first intermolecular and the second intramolecular, instead of the classical macrolactonization methods.

  DOI：

  10.1021/jo970020s
• 作为产物：
  描述：

  (E,5S)-5-[tert-butyl(diphenyl)silyl]oxy-1,1-diethoxyhex-3-en-2-one 在 dimethyl sulfide borane 、 bis(trifluoroethyl) n-butylboronate 、 (R)-(+)-alpha,alpha-二苯基脯氨醇 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (E)-(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxy)-1,1-diethoxy-hex-3-en-2-ol
  参考文献：
  名称：

  Enantioselective Total Synthesis of the (−)-(6R,11R,14S)-Isomer of Colletallol

  摘要：

  The total synthesis of the (-)-(6R,11R,14S)-isomer of colletallol was achieved in 15 steps. The key steps of the sequence were the building of the macrocycle via two consecutive Wittig reactions, the first intermolecular and the second intramolecular, instead of the classical macrolactonization methods.

  DOI：

  10.1021/jo970020s

文献信息

• (5S)-1,1-diethoxy-5-t-butyldiphenylsilyloxy-hex-3-en-2-one: A new functionalized versatile chiral building block
  作者：Hervé Dumartin、Yves Le Floc'h、René Grée

  DOI：10.1016/s0040-4039(00)73467-8

  日期：1994.9

  The title enone 3 is easily prepared from protected lactaldehyde. Highly diastereoselective reduction of 3 is only obtained with CBS reagents.
• Enantioselective Total Synthesis of the (−)-(6<i>R</i>,11<i>R</i>,14<i>S</i>)-Isomer of Colletallol
  作者：Sonia J. Amigoni、Loïc J. Toupet、Yves J. Le Floc'h

  DOI：10.1021/jo970020s

  日期：1997.9.1

  The total synthesis of the (-)-(6R,11R,14S)-isomer of colletallol was achieved in 15 steps. The key steps of the sequence were the building of the macrocycle via two consecutive Wittig reactions, the first intermolecular and the second intramolecular, instead of the classical macrolactonization methods.