methyl 4-(4-((2S,3R,8R,10R,E)-2-((tert-butoxycarbonyl)(methyl)amino)-3-((tert-butyldimethylsilyl)oxy)-8,10-dimethyldodec-6-en-1-yl)phenoxy)butanoate | 1246843-39-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-(4-((2S,3R,8R,10R,E)-2-((tert-butoxycarbonyl)(methyl)amino)-3-((tert-butyldimethylsilyl)oxy)-8,10-dimethyldodec-6-en-1-yl)phenoxy)butanoate
• CAS: 1246843-39-9
• 化学式: C₃₇H₆₅NO₆Si
• 分子量: 648.012
• InChiKey: QNGGAKXGQVBGAF-OCHMDYBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  45.0
• 可旋转键数：
  18.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  74.3
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 4-(4-((2S,3R,8R,10R,E)-2-((tert-butoxycarbonyl)(methyl)amino)-3-((tert-butyldimethylsilyl)oxy)-8,10-dimethyldodec-6-en-1-yl)phenoxy)butanoate 在 barium hydroxide octahydrate 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 35.0h， 以91%的产率得到4-(4-((2S,3R,8R,10R,E)-2-((tert-butoxycarbonyl)(methyl)amino)-3-((tert-butyldimethylsilyl)oxy)-8,10-dimethyldodec-6-en-1-yl)phenoxy)butanoic acid
  参考文献：
  名称：

  Total Synthesis and Biological Evaluation of Tyroscherin

  摘要：

  The efficient synthesis and biological evaluation of both the reported and revised structures of tyroscherin have been achieved. Central to our synthesis is a cross metathesis reaction that generated the trans-olefin regioselectively. This synthetic strategy enabled the facile manipulation of tyroscherin stereochemistry, facilitating the generation of all 16 tyroscherin diastereomers and a photoactivatable tyroscherin-based affinity probe for future mode of action studies.

  DOI：

  10.1021/ol101801u
• 作为产物：
  描述：

  4-溴丁酸甲酯 、 tert-butyl ((2S,3R,8R,10R,E)-3-((tert-butyldimethylsilyl)oxy)-1-(4-hydroxyphenyl)-8,10-dimethyldodec-6-en-2-yl)(methyl)carbamate 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 19.0h， 以92%的产率得到methyl 4-(4-((2S,3R,8R,10R,E)-2-((tert-butoxycarbonyl)(methyl)amino)-3-((tert-butyldimethylsilyl)oxy)-8,10-dimethyldodec-6-en-1-yl)phenoxy)butanoate
  参考文献：
  名称：

  Total Synthesis and Biological Evaluation of Tyroscherin

  摘要：

  The efficient synthesis and biological evaluation of both the reported and revised structures of tyroscherin have been achieved. Central to our synthesis is a cross metathesis reaction that generated the trans-olefin regioselectively. This synthetic strategy enabled the facile manipulation of tyroscherin stereochemistry, facilitating the generation of all 16 tyroscherin diastereomers and a photoactivatable tyroscherin-based affinity probe for future mode of action studies.

  DOI：

  10.1021/ol101801u