(E,2S,4S,8S)-10-[(2R,3S,4S,5S,6R)-6-[2-(bromomethyl)-6-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethoxy-4-methylphenyl]-4-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethyloxan-2-yl]-2,4,6,8-tetramethyldec-6-enal | 1054608-32-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (E,2S,4S,8S)-10-[(2R,3S,4S,5S,6R)-6-[2-(bromomethyl)-6-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethoxy-4-methylphenyl]-4-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethyloxan-2-yl]-2,4,6,8-tetramethyldec-6-enal
• CAS: 1054608-32-0
• 化学式: C₄₃H₇₇BrO₆Si₂
• 分子量: 826.156
• InChiKey: SSWCENUOXWBBJA-CDOFGBIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.01
• 重原子数：
  52
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E,2S,4S,8S)-10-[(2R,3S,4S,5S,6R)-6-[2-(bromomethyl)-6-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethoxy-4-methylphenyl]-4-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethyloxan-2-yl]-2,4,6,8-tetramethyldec-6-enal 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 以0.081 g的产率得到(1R,9R,10S,12S,14E,16S,19R,20S,21S,22S)-3,21-bis[[tert-butyl(dimethyl)silyl]oxy]-4,6-dimethoxy-5,10,12,14,16,20,22-heptamethyl-23-oxatricyclo[17.3.1.02,7]tricosa-2(7),3,5,14-tetraen-9-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：

  (2S,4S,8S,E)-10-((2R,3S,4S,5S,6R)-6-(2-(bromomethyl)-6-(tert-butyldimethylsilyloxy)-3,5-dimethoxy-4-methylphenyl)-4-(tert-butyldimethylsilyloxy)-3,5-dimethyltetrahydro-2H-pyran-2-yl)-2,4,6,8-tetramethyldec-6-en-1ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (E,2S,4S,8S)-10-[(2R,3S,4S,5S,6R)-6-[2-(bromomethyl)-6-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethoxy-4-methylphenyl]-4-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethyloxan-2-yl]-2,4,6,8-tetramethyldec-6-enal
  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.