[(1R,3S,5R,10S,12R,15S,17S,19R,22R,24S)-21,21-bis(ethylsulfanyl)-22-(hydroxymethyl)-2,6,11,18,23-pentaoxapentacyclo[15.9.0.03,12.05,10.019,24]hexacosan-15-yl] acetate | 208454-59-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: [(1R,3S,5R,10S,12R,15S,17S,19R,22R,24S)-21,21-bis(ethylsulfanyl)-22-(hydroxymethyl)-2,6,11,18,23-pentaoxapentacyclo[15.9.0.03,12.05,10.019,24]hexacosan-15-yl] acetate
• CAS: 208454-59-5
• 化学式: C₂₈H₄₆O₈S₂
• 分子量: 574.8
• InChiKey: IXXJQYLNHTYLBG-GRBCIZHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  143
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(1R,3S,5R,10S,12R,15S,17S,19R,22R,24S)-21,21-bis(ethylsulfanyl)-22-(hydroxymethyl)-2,6,11,18,23-pentaoxapentacyclo[15.9.0.03,12.05,10.019,24]hexacosan-15-yl] acetate 在 三氧化硫吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 0.5h， 生成 [(1R,3S,5R,10S,12R,15S,17S,19R,22R,24S)-21,21-bis(ethylsulfanyl)-22-formyl-2,6,11,18,23-pentaoxapentacyclo[15.9.0.03,12.05,10.019,24]hexacosan-15-yl] acetate
  参考文献：
  名称：

  A Convergent Synthesis of the Decacyclic Ciguatoxin Model Containing the F−M Ring Framework

  摘要：

  A highly convergent synthesis of the decacyclic ciguatoxin model 2, which contains the F-M ring framework of the natural product, has been achieved through the assembly of pentacyclic oxonane 4 and JKLM ring fragment 5. The two key steps in the synthesis of the former compound are (i) a Lewis acid-mediated intramolecular reaction of a gamma-alkoxyallylsilane with an acetal group to form an O-linked oxacycle and (ii) a SmI2-mediated intramolecular Reformatsky reaction leading to construction of the annelated oxonane ring system. Preliminary biological investigations revealed that model compound 2 did not inhibit the binding of tritium-labeled dihydrobrevetoxin B to voltage-sensitive sodium channels at micromolar concentrations.

  DOI：

  10.1021/jo990989b
• 作为产物：
  描述：

  在 咪唑 、 草酰氯 、 四丁基氟化铵 、 四氯化钛 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 [(1R,3S,5R,10S,12R,15S,17S,19R,22R,24S)-21,21-bis(ethylsulfanyl)-22-(hydroxymethyl)-2,6,11,18,23-pentaoxapentacyclo[15.9.0.03,12.05,10.019,24]hexacosan-15-yl] acetate
  参考文献：
  名称：

  A Convergent Synthesis of the Decacyclic Ciguatoxin Model Containing the F−M Ring Framework

  摘要：

  A highly convergent synthesis of the decacyclic ciguatoxin model 2, which contains the F-M ring framework of the natural product, has been achieved through the assembly of pentacyclic oxonane 4 and JKLM ring fragment 5. The two key steps in the synthesis of the former compound are (i) a Lewis acid-mediated intramolecular reaction of a gamma-alkoxyallylsilane with an acetal group to form an O-linked oxacycle and (ii) a SmI2-mediated intramolecular Reformatsky reaction leading to construction of the annelated oxonane ring system. Preliminary biological investigations revealed that model compound 2 did not inhibit the binding of tritium-labeled dihydrobrevetoxin B to voltage-sensitive sodium channels at micromolar concentrations.

  DOI：

  10.1021/jo990989b