tert-butyl (S,E)-5-(N-(benzoyloxy)-5-((tert-butyldiphenylsilyl)oxy)-3-methylpent-2-enamido)-2-((tert-butoxycarbonyl)amino)pentanoate | 1224926-52-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (S,E)-5-(N-(benzoyloxy)-5-((tert-butyldiphenylsilyl)oxy)-3-methylpent-2-enamido)-2-((tert-butoxycarbonyl)amino)pentanoate
• CAS: 1224926-52-6
• 化学式: C₄₃H₅₈N₂O₈Si
• 分子量: 759.028
• InChiKey: DWWKOVNQFVZONZ-LKFOBHHFSA-N

物化性质

• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.52
• 重原子数：
  54.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  120.47
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  tert-butyl (R)-5-((benzoyloxy)amino)-2-((tert-butoxycarbonyl)amino)pentanoate 、 (2E)-5-(tert-butyldiphenylsilyloxy)-3-methylpent-2-enoic acid 在 氯化亚砜 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以4%的产率得到tert-butyl (S,E)-5-(N-(benzoyloxy)-5-((tert-butyldiphenylsilyl)oxy)-3-methylpent-2-enamido)-2-((tert-butoxycarbonyl)amino)pentanoate
  参考文献：
  名称：

  Synthesis of the trans-fusarinine scaffold

  摘要：

  The trans-fusarinine backbone is a common feature encountered in many fungal siderophores. This monomer is notably the structural base of N-alpha-methyl coprogen B and dimerumic acid. Both siderophores are known to be secreted by Scedosporium apiospermum, an emerging pathogenic fungus studied for its high involvement in invasive infections of immunocompromised patients. The strategy developed here for the synthesis of the trans-fusarinine scaffold relies on the preparation of both N-hydroxyornithine and 3-anhydroxymevalonic acid subunits starting from L-ornithine and 3-butyn-1-ol, respectively. The coupling of these two building blocks led to the expected protected backbone. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.058