| 208454-63-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• CAS: 208454-63-1
• 化学式: C₄₄H₆₈O₁₄
• 分子量: 821.016
• InChiKey: YWDNTOAEANNJFU-PWIOPQFDSA-N

反应信息

• 作为反应物：
  描述：

  叔丁基二甲硅基三氟甲磺酸酯 、 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成
  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：

  [(1R,3S,4'S,5R,7S,9R,10S,11S,12R,14S,15S,16S,17R,19S,21Z,23R,25S,28R,30S,32R,37S,39R,42S,44S)-10,11,16-trimethyl-4',15-bis(phenylmethoxy)spiro[4,8,13,18,24,29,33,38,45-nonaoxanonacyclo[23.20.0.03,23.05,19.07,17.09,14.028,44.030,39.032,37]pentatetracont-21-ene-12,2'-oxolane]-42-yl] acetate 在 palladium dihydroxide 氢气 、 溶剂黄146 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 12.0h， 生成
  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