5-(3,6-bis(tert-butyldimethylsilyloxy)hex-4-ynyl)-2-((2S,3R)-3-(iodomethyl)aziridin-2-yl)oxazole | 958299-55-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(3,6-bis(tert-butyldimethylsilyloxy)hex-4-ynyl)-2-((2S,3R)-3-(iodomethyl)aziridin-2-yl)oxazole
• 英文别名: tert-butyl-[4-[tert-butyl(dimethyl)silyl]oxy-6-[2-[(2S,3R)-3-(iodomethyl)aziridin-2-yl]-1,3-oxazol-5-yl]hex-2-ynoxy]-dimethylsilane
• CAS: 958299-55-3
• 化学式: C₂₄H₄₃IN₂O₃Si₂
• 分子量: 590.693
• InChiKey: MNSCLQROMUCNFJ-LLQWEQGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.47
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(3,6-bis(tert-butyldimethylsilyloxy)hex-4-ynyl)-2-((2S,3R)-3-(iodomethyl)aziridin-2-yl)oxazole 、 三氟甲磺酸叔丁基二苯基硅烷基酯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以92%的产率得到5-(3,6-bis(tert-butyldimethylsilyloxy)hex-4-ynyl)-2-((2S,3R)-1-(tert-butyldiphenylsilyl)-3-(iodomethyl)aziridin-2-yl)oxazole
  参考文献：
  名称：

  N-Silyl Protecting Groups for Labile Aziridines:  Application toward the Synthesis of N-H Aziridinomitosenes

  摘要：

  Hindered N-silylarnines were examined for their utility to serve as protecting groups for the labile aziridine nitrogen found within the highly sensitive aziridinomitosene framework. tert-Butyldiphenylsilyl and modified tert-butyldiphenylsilyl groups were the most resistant to nitrogen- silicon bond cleavage under various reaction conditions and were thus employed in transformations relevant to aziridinomitosene synthesis. The N-silylaziridines 7a, 21a, and 21b underwent azomethine ylide cycloaddition and afforded, upon deprotection, the N-H aziridine 24 in 18-32% overall yield for the three steps.

  DOI：

  10.1021/jo7013615
• 作为产物：
  描述：

  (2S,3R)-2-[5-[3,6-bis-(tert-butyldimethylsilyloxy)-4-hexynyl]oxazol-2-yl]-3-iodomethyl-1-tritylaziridine 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以95%的产率得到5-(3,6-bis(tert-butyldimethylsilyloxy)hex-4-ynyl)-2-((2S,3R)-3-(iodomethyl)aziridin-2-yl)oxazole
  参考文献：
  名称：

  N-Silyl Protecting Groups for Labile Aziridines:  Application toward the Synthesis of N-H Aziridinomitosenes

  摘要：

  Hindered N-silylarnines were examined for their utility to serve as protecting groups for the labile aziridine nitrogen found within the highly sensitive aziridinomitosene framework. tert-Butyldiphenylsilyl and modified tert-butyldiphenylsilyl groups were the most resistant to nitrogen- silicon bond cleavage under various reaction conditions and were thus employed in transformations relevant to aziridinomitosene synthesis. The N-silylaziridines 7a, 21a, and 21b underwent azomethine ylide cycloaddition and afforded, upon deprotection, the N-H aziridine 24 in 18-32% overall yield for the three steps.

  DOI：

  10.1021/jo7013615