(1S,2S,4R,5S,6S)-methyl-4-(2-(benzyloxy)-3,5-dimethoxy-4-methylphenyl)-1,5-dimethyl-3,7-dioxabicyclo[4.1.0]heptane-2-carboxylate | 1054608-55-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,4R,5S,6S)-methyl-4-(2-(benzyloxy)-3,5-dimethoxy-4-methylphenyl)-1,5-dimethyl-3,7-dioxabicyclo[4.1.0]heptane-2-carboxylate
• 英文别名: methyl (1S,2S,4R,5S,6S)-4-(3,5-dimethoxy-4-methyl-2-phenylmethoxyphenyl)-1,5-dimethyl-3,7-dioxabicyclo[4.1.0]heptane-2-carboxylate
• CAS: 1054608-55-7
• 化学式: C₂₅H₃₀O₇
• 分子量: 442.509
• InChiKey: TXTBAGWWBBRJIA-XUIHROFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  75.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S,2S,4R,5S,6S)-methyl-4-(2-(benzyloxy)-3,5-dimethoxy-4-methylphenyl)-1,5-dimethyl-3,7-dioxabicyclo[4.1.0]heptane-2-carboxylate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以65%的产率得到(2R,3R,4S)-methyl-2-(2-(benzyloxy)-3,5-dimethoxy-4-methylphenyl)-4-hydroxy-3,5-dimethyl-3,4-dihydro-2H-pyran-6-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：

  (2S,5R,6R)-methyl-6-(2-(benzyloxy)-3,5-dimethoxy-4-methylphenyl)-3,5-dimethyl-5,6-dihydro-2H-pyran-2-carboxylate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以54%的产率得到(1R,2S,4R,5S,6R)-methyl-4-(2-(benzyloxy)-3,5-dimethoxy-4-methylphenyl)-1,5-dimethyl-3,7-dioxabicyclo[4.1.0]heptane-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.