(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 | 1054608-71-7

• 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: (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
• CAS: 1054608-71-7
• 化学式: C₄₉H₉₄O₇Si₃
• 分子量: 879.538
• InChiKey: YSCRIXWWWRGRID-UWLOYNPUSA-N

物化性质

• 沸点：
  763.6±60.0 °C(predicted)
• 密度：
  0.97±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.43
• 重原子数：
  59.0
• 可旋转键数：
  19.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  75.61
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (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 在 咪唑 、 溴 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到(3-(bromomethyl)-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-methylphenoxy)(tert-butyl)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
• 作为产物：
  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