(2S,3S,4R,5S,6R)-methyl-4-(tert-butyldimethylsilyloxy)-6-(2-(tert-butyldimethylsilyloxy)-6-(hydroxymethyl)-3,5-dimethoxy-4-methylphenyl)-3,5-dimethyltetrahydro-2H-pyran-2-carboxylate | 1054608-65-9

• 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)-6-(hydroxymethyl)-3,5-dimethoxy-4-methylphenyl)-3,5-dimethyltetrahydro-2H-pyran-2-carboxylate
• CAS: 1054608-65-9
• 化学式: C₃₁H₅₆O₈Si₂
• 分子量: 612.952
• InChiKey: UQIPLUWMMVEBFE-YPWSKOBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.16
• 重原子数：
  41.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  92.68
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5S,6R)-methyl-4-(tert-butyldimethylsilyloxy)-6-(2-(tert-butyldimethylsilyloxy)-6-(hydroxymethyl)-3,5-dimethoxy-4-methylphenyl)-3,5-dimethyltetrahydro-2H-pyran-2-carboxylate 、 氯甲基甲基醚 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到(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
  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-4-methyl-6-vinylphenyl)-3,5-dimethyltetrahydro-2H-pyran-2-carboxylate 在 吡啶 、 Sudan Red B 、 臭氧 、 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以89%的产率得到(2S,3S,4R,5S,6R)-methyl-4-(tert-butyldimethylsilyloxy)-6-(2-(tert-butyldimethylsilyloxy)-6-(hydroxymethyl)-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