(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 | 1054608-34-2

• 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: (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
• 英文别名: (2S,3S,4R,5S,6R)-4-[tert-butyl(dimethyl)silyl]oxy-6-[2-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethoxy-6-(methoxymethoxymethyl)-4-methylphenyl]-3,5-dimethyloxane-2-carbaldehyde
• CAS: 1054608-34-2
• 化学式: C₃₂H₅₈O₈Si₂
• 分子量: 626.979
• InChiKey: ICHIGQPYPZHCNF-BBUVEYNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.82
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (2S,3S,4R,5S,6R)-methyl-4-(tert-butyldimethylsilyloxy)-6-(2-(tert-butyldimethylsilyloxy)-3,5-dimethoxy-6-((methoxymethoxy)methyl)-4-methylphenyl)-3,5-dimethyltetrahydro-2H-pyran-2-carboxylate 在 二异丁基氢化铝 、 rochelle salt 作用下， 以 乙醚 、 正己烷 为溶剂， 以98%的产率得到(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
  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.