(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 | 1054608-30-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (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
• CAS: 1054608-30-8
• 化学式: C₄₃H₇₈O₆Si₂
• 分子量: 747.26
• InChiKey: KVDOHOLAFWLWJY-AMGXFAQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.83
• 重原子数：
  51
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (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 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以86%的产率得到(12R,13S,14S,15S,16R,4R,5S,7S,11S,E)-14-((tert-butyldimethylsilyl)oxy)-23,25-dimethoxy-13,15,24,5,7,9,11-heptamethyl-13,14,15,16-tetrahydro-12H-1(2,6)-pyrana-2(1,2)-benzenacyclotridecaphan-9-ene-26,4-diol
  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：

  (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

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.