(2-((2S,3S,4R,5S,6R)-6-((S,Z)-4-(benzyloxy)-3-methylbut-1-enyl)-4-(tert-butyldimethylsilyloxy)-3,5-dimethyltetrahydro-2H-pyran-2-yl)-4,6-dimethoxy-3-((methoxymethoxy)methyl)-5-methylphenoxy)(tert-butyl)dimethylsilane | 1054608-68-2

• 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: (2-((2S,3S,4R,5S,6R)-6-((S,Z)-4-(benzyloxy)-3-methylbut-1-enyl)-4-(tert-butyldimethylsilyloxy)-3,5-dimethyltetrahydro-2H-pyran-2-yl)-4,6-dimethoxy-3-((methoxymethoxy)methyl)-5-methylphenoxy)(tert-butyl)dimethylsilane
• 英文别名: tert-butyl-[(2R,3S,4S,5S,6R)-2-[2-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethoxy-6-(methoxymethoxymethyl)-4-methylphenyl]-3,5-dimethyl-6-[(Z,3S)-3-methyl-4-phenylmethoxybut-1-enyl]oxan-4-yl]oxy-dimethylsilane
• CAS: 1054608-68-2
• 化学式: C₄₃H₇₂O₈Si₂
• 分子量: 773.211
• InChiKey: UCNDVANEIPBBFD-UKCROARHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.03
• 重原子数：
  53
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (2-((2S,3S,4R,5S,6R)-6-((S,Z)-4-(benzyloxy)-3-methylbut-1-enyl)-4-(tert-butyldimethylsilyloxy)-3,5-dimethyltetrahydro-2H-pyran-2-yl)-4,6-dimethoxy-3-((methoxymethoxy)methyl)-5-methylphenoxy)(tert-butyl)dimethylsilane 在 氢气 、 镍 作用下， 以 乙醇 为溶剂， 反应 96.0h， 以98%的产率得到(S)-4-((2R,3S,4S,5S,6R)-4-(tert-butyldimethylsilyloxy)-6-(2-(tert-butyldimethylsilyloxy)-3,5-dimethoxy-6-((methoxymethoxy)methyl)-4-methylphenyl)-3,5-dimethyltetrahydro-2H-pyran-2-yl)-2-methylbutan-1-ol
  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：

  ((R)-3-benzyloxy-2-methylpropyl)triphenylphosphonium bromide 、 (2S,3S,4R,5S,6R)-4-(tert-butyldimethylsilyloxy)-6-(2-(tert-butyldimethylsilyloxy)-3,5-dimethoxy-6-((methoxymethoxy)methyl)-4-methylphenyl)-3,5-dimethyl tetrahydro-2H-pyran-2-carbaldehyde 在 正丁基锂 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以81%的产率得到(2-((2S,3S,4R,5S,6R)-6-((S,Z)-4-(benzyloxy)-3-methylbut-1-enyl)-4-(tert-butyldimethylsilyloxy)-3,5-dimethyltetrahydro-2H-pyran-2-yl)-4,6-dimethoxy-3-((methoxymethoxy)methyl)-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

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.