(2S,4S,6R)-2-((2R,3R)-3-((3S)-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 | 1213265-30-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (2S,4S,6R)-2-((2R,3R)-3-((3S)-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
• CAS: 1213265-30-5
• 化学式: C₅₉H₁₁₅NO₁₀Si₅
• 分子量: 1138.99
• InChiKey: UFTWRDFMYFPECK-ILFLQQRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.21
• 重原子数：
  75.0
• 可旋转键数：
  24.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  120.01
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2,2-dimethylpropanoyl (2S,3S)-3-methoxy-5-methyl-2-(2-trimethylsilylethoxymethoxy)hex-5-enoate 、 (2S,4S,6R)-2-((2R,3R)-3-((3S)-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， 生成 11,15-bis(tert-butyldimethylsilyl)-21,23-bistriisopropylsilyl-7-N-(2-(trimethylsilyl)ethoxycarbonyl)-5-(trimethylsilyl)ethoxymethylirciniastatin A
  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：

  2-(三甲硅基)乙醇 、 以 甲苯 为溶剂， 反应 17.0h， 生成 (2S,4S,6R)-2-((2R,3R)-3-((3S)-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
  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