(2S,3S,4R,5S,6R)-methyl-4-(tert-butyldimethylsilyloxy)-6-(2-(tert-butyldimethylsilyloxy)-3,5-dimethoxy-4-methylphenyl)-3,5-dimethyltetrahydro-2H-pyran-2-carboxylate | 1054608-41-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4R,5S,6R)-methyl-4-(tert-butyldimethylsilyloxy)-6-(2-(tert-butyldimethylsilyloxy)-3,5-dimethoxy-4-methylphenyl)-3,5-dimethyltetrahydro-2H-pyran-2-carboxylate
• 英文别名: methyl (2S,3S,4R,5S,6R)-4-[tert-butyl(dimethyl)silyl]oxy-6-[2-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethoxy-4-methylphenyl]-3,5-dimethyloxane-2-carboxylate
• CAS: 1054608-41-1
• 化学式: C₃₀H₅₄O₇Si₂
• 分子量: 582.926
• InChiKey: JGXFPOVDMOCHBF-DRLWGBRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.67
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5S,6R)-methyl-4-(tert-butyldimethylsilyloxy)-6-(2-(tert-butyldimethylsilyloxy)-3,5-dimethoxy-4-methylphenyl)-3,5-dimethyltetrahydro-2H-pyran-2-carboxylate 在 溴 、 methyloxirane 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到(2S,3S,4R,5S,6R)-methyl-6-(2-bromo-6-(tert-butyldimethylsilyloxy)-3,5-dimethoxy-4-methylphenyl)-4-(tert-butyldimethylsilyloxy)-3,5-dimethyltetrahydro-2H-pyran-2-carboxylate
  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：

  (2R,3R,4R)-methyl-2-(2-(benzyloxy)-3,5-dimethoxy-4-methylphenyl)-4-hydroxy-3,5-dimethyl-3,4-dihydro-2H-pyran-6-carboxylate 、 叔丁基二甲硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到(2S,3S,4R,5S,6R)-methyl-4-(tert-butyldimethylsilyloxy)-6-(2-(tert-butyldimethylsilyloxy)-3,5-dimethoxy-4-methylphenyl)-3,5-dimethyltetrahydro-2H-pyran-2-carboxylate
  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.