| 158478-19-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• CAS: 158478-19-4
• 化学式: C₂₃H₃₀O₃Si
• 分子量: 382.575
• InChiKey: MVOMFSLARUETQW-VHEBQXMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  在 lithium hydroxide 作用下， 以 叔丁醇 为溶剂， 以100%的产率得到(2E)-5-(tert-butyldiphenylsilyloxy)-3-methylpent-2-enoic acid
  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
• 作为产物：
  描述：

  methyl copper bromide 、 methyl (Z)-5-tert-butyldiphenylsilyloxy-3-phenylsulfanylpent-2-enoate 以 四氢呋喃 为溶剂， 以99%的产率得到
  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