tert-butyl((2R,3S,4S,5S,6R)-2-((3S,7S,9S,E)-10-(tert-butyldimethylsilyloxy)-3,5,7,9-tetramethyldec-4-enyl)-6-(2-(tert-butyldimethylsilyloxy)-3,5-dimethoxy-6-((methoxymethoxy)methyl)-4-methylphenyl)-3,5-dimethyltetrahydro-2H-pyran-4-yloxy)dimethylsilane | 1054608-51-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: tert-butyl((2R,3S,4S,5S,6R)-2-((3S,7S,9S,E)-10-(tert-butyldimethylsilyloxy)-3,5,7,9-tetramethyldec-4-enyl)-6-(2-(tert-butyldimethylsilyloxy)-3,5-dimethoxy-6-((methoxymethoxy)methyl)-4-methylphenyl)-3,5-dimethyltetrahydro-2H-pyran-4-yloxy)dimethylsilane
• 英文别名: tert-butyl-[(E,2S,4S,8S)-10-[(2R,3S,4S,5S,6R)-4-[tert-butyl(dimethyl)silyl]oxy-6-[2-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethoxy-6-(methoxymethoxymethyl)-4-methylphenyl]-3,5-dimethyloxan-2-yl]-2,4,6,8-tetramethyldec-6-enoxy]-dimethylsilane
• CAS: 1054608-51-3
• 化学式: C₅₁H₉₈O₈Si₃
• 分子量: 923.591
• InChiKey: PUJNHORPENBHRW-VIBGSJEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.06
• 重原子数：
  62
• 可旋转键数：
  25
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl((2R,3S,4S,5S,6R)-2-((3S,7S,9S,E)-10-(tert-butyldimethylsilyloxy)-3,5,7,9-tetramethyldec-4-enyl)-6-(2-(tert-butyldimethylsilyloxy)-3,5-dimethoxy-6-((methoxymethoxy)methyl)-4-methylphenyl)-3,5-dimethyltetrahydro-2H-pyran-4-yloxy)dimethylsilane 在 乙醚 、 乙硫醇 作用下， 以 乙醚 为溶剂， 反应 48.0h， 以91%的产率得到(3-(tert-butyldimethylsilyloxy)-2-((2R,3S,4S,5S,6R)-4-(tert-butyldimethylsilyloxy)-6-((3S,7S,9S,E)-10-(tert-butyldimethylsilyloxy)-3,5,7,9-tetramethyldec-4-enyl)-3,5-dimethyltetrahydro-2H-pyran-2-yl)-4,6-dimethoxy-5-methylphenyl)methanol
  参考文献：
  名称：

  Total Synthesis of (−)-Kendomycin

  摘要：

  An enantioselective synthesis of (-)-kendomycin is described and is based on the application of the organosilane-based [4 + 2]-annulation strategy for the assembly of the C1a-C10 fragment. An underutilized samarium(II) iodide-assisted cyclization (intramolecular Barbier-type reaction) is employed to afford the protected macrocycle.

  DOI：

  10.1021/ol801499s
• 作为产物：
  描述：

  tert-butyl((2S,4S)-5-iodo-2,4-dimethylpentyloxy)dimethylsilane 、 tert-butyl((2R,3S,4S,5S,6R)-2-(2-(tert-butyldimethylsilyloxy)-3,5-dimethoxy-6-((methoxymethoxy)methyl)-4-methylphenyl)-6-((S,E)-5-iodo-3-methylhex-4-enyl)-3,5-dimethyltetrahydro-2H-pyran-4-yloxy)dimethylsilane 在 叔丁基锂 、 zinc(II) chloride 、 四(三苯基膦)钯 作用下， 以 乙醚 、 正戊烷 、 四氢呋喃 为溶剂， 反应 0.17h， 以92%的产率得到tert-butyl((2R,3S,4S,5S,6R)-2-((3S,7S,9S,E)-10-(tert-butyldimethylsilyloxy)-3,5,7,9-tetramethyldec-4-enyl)-6-(2-(tert-butyldimethylsilyloxy)-3,5-dimethoxy-6-((methoxymethoxy)methyl)-4-methylphenyl)-3,5-dimethyltetrahydro-2H-pyran-4-yloxy)dimethylsilane
  参考文献：
  名称：

  Total Synthesis of (−)-Kendomycin

  摘要：

  An enantioselective synthesis of (-)-kendomycin is described and is based on the application of the organosilane-based [4 + 2]-annulation strategy for the assembly of the C1a-C10 fragment. An underutilized samarium(II) iodide-assisted cyclization (intramolecular Barbier-type reaction) is employed to afford the protected macrocycle.

  DOI：

  10.1021/ol801499s

文献信息

• Total Synthesis of (−)-Kendomycin
  作者：Jason T. Lowe、James S. Panek

  DOI：10.1021/ol801499s

  日期：2008.9.1

  An enantioselective synthesis of (-)-kendomycin is described and is based on the application of the organosilane-based [4 + 2]-annulation strategy for the assembly of the C1a-C10 fragment. An underutilized samarium(II) iodide-assisted cyclization (intramolecular Barbier-type reaction) is employed to afford the protected macrocycle.