11,15-bis(tert-butyldimethylsilyl)-21,23-bis(triisopropylsilyl)-1-triethylsilyl-7-N-(2-(trimethylsilyl)ethoxycarbonyl)-5-(trimethylsilyl)ethoxymethylalkymberin | 1213265-40-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: 11,15-bis(tert-butyldimethylsilyl)-21,23-bis(triisopropylsilyl)-1-triethylsilyl-7-N-(2-(trimethylsilyl)ethoxycarbonyl)-5-(trimethylsilyl)ethoxymethylalkymberin
• CAS: 1213265-40-7
• 化学式: C₇₈H₁₅₁NO₁₄Si₇
• 分子量: 1523.65
• InChiKey: OLUDKFDSXWNQQQ-AQMHSMRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.61
• 重原子数：
  100.0
• 可旋转键数：
  37.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  155.98
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  11,15-bis(tert-butyldimethylsilyl)-21,23-bis(triisopropylsilyl)-1-triethylsilyl-7-N-(2-(trimethylsilyl)ethoxycarbonyl)-5-(trimethylsilyl)ethoxymethylalkymberin 在 三(二甲氨基)锍二氟三甲基硅酸 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以54%的产率得到(+)-alkymberin
  参考文献：
  名称：

  Syntheses and Biological Evaluation of Irciniastatin A and the C1−C2 Alkyne Analogue

  摘要：

  Syntheses of both natural (+)- and unnatural (-)-irciniastatin A (aka psymberin) as well as a C1-C2 alkyne analogue of (+)-irciniastatin A have been achieved. The key features of the syntheses include a highly regioselective epoxide-opening reaction and a late-stage assembly of C1-C6, C8-C16, and C17-C25 fragments. (+)-Alkymberin retained a high level of cytotoxicity, whereas (-)-irciniastatin A showed almost no activity. These results suggest that (+)-alkymberin could be a useful enantio-differential probe for mode-of-action study.

  DOI：

  10.1021/ol1000389
• 作为产物：
  描述：

  C₂₄H₄₈O₅Si₂ 、 (2R,4R,6S)-2-((2S,3S)-3-((3R)-6,8-bistriisopropylsilyloxy-5-methyl-3,4-dihydroisocoumarinyl)-3-methyl-2-tert-butyldimethylsilyloxypropyl)-3,3-dimethyl-6-((S)-methoxy-(N-(2-(trimethylsilyl)ethoxycarbonyl)amino)-methyl)-4-tert-butyldimethylsilyloxytetrahydropyran 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以20.8 mg的产率得到11,15-bis(tert-butyldimethylsilyl)-21,23-bis(triisopropylsilyl)-1-triethylsilyl-7-N-(2-(trimethylsilyl)ethoxycarbonyl)-5-(trimethylsilyl)ethoxymethylalkymberin
  参考文献：
  名称：

  Syntheses and Biological Evaluation of Irciniastatin A and the C1−C2 Alkyne Analogue

  摘要：

  Syntheses of both natural (+)- and unnatural (-)-irciniastatin A (aka psymberin) as well as a C1-C2 alkyne analogue of (+)-irciniastatin A have been achieved. The key features of the syntheses include a highly regioselective epoxide-opening reaction and a late-stage assembly of C1-C6, C8-C16, and C17-C25 fragments. (+)-Alkymberin retained a high level of cytotoxicity, whereas (-)-irciniastatin A showed almost no activity. These results suggest that (+)-alkymberin could be a useful enantio-differential probe for mode-of-action study.

  DOI：

  10.1021/ol1000389