1-[(2S,3S,4aR,8aS)-3-[[(2R,3S,4aR,6S,7R,9aS)-6-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-3-[tert-butyl(diphenyl)silyl]oxy-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,4,4a,6,7,8,9,9a-octahydro-2H-pyrano[3,2-b]oxepin-7-yl]oxy]-2,3,4,4a,6,7,8,8a-octahydropyrano[3,2-b]pyran-2-yl]ethanone | 208454-53-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[(2S,3S,4aR,8aS)-3-[[(2R,3S,4aR,6S,7R,9aS)-6-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-3-[tert-butyl(diphenyl)silyl]oxy-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,4,4a,6,7,8,9,9a-octahydro-2H-pyrano[3,2-b]oxepin-7-yl]oxy]-2,3,4,4a,6,7,8,8a-octahydropyrano[3,2-b]pyran-2-yl]ethanone
• CAS: 208454-53-9
• 化学式: C₆₀H₈₆O₉Si₃
• 分子量: 1035.59
• InChiKey: HDQRIJDOAWERGG-ARBJJLMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  72
• 可旋转键数：
  19
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  90.9
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-[(2S,3S,4aR,8aS)-3-[[(2R,3S,4aR,6S,7R,9aS)-6-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-3-[tert-butyl(diphenyl)silyl]oxy-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,4,4a,6,7,8,9,9a-octahydro-2H-pyrano[3,2-b]oxepin-7-yl]oxy]-2,3,4,4a,6,7,8,8a-octahydropyrano[3,2-b]pyran-2-yl]ethanone 在 N-溴代丁二酰亚胺(NBS) 、 samarium diiodide 、 camphor-10-sulfonic acid 、 三氧化硫吡啶 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 3.33h， 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：

  在 lead(IV) acetate 、 四氧化锇 、 草酰氯 、 二甲基亚砜 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 叔丁醇 、 苯 为溶剂， 反应 0.5h， 生成 1-[(2S,3S,4aR,8aS)-3-[[(2R,3S,4aR,6S,7R,9aS)-6-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-3-[tert-butyl(diphenyl)silyl]oxy-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,4,4a,6,7,8,9,9a-octahydro-2H-pyrano[3,2-b]oxepin-7-yl]oxy]-2,3,4,4a,6,7,8,8a-octahydropyrano[3,2-b]pyran-2-yl]ethanone
  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

文献信息

• A Convergent Synthesis of the Decacyclic Ciguatoxin Model Containing the F−M Ring Framework
  作者：Masayuki Inoue、Makoto Sasaki、Kazuo Tachibana

  DOI：10.1021/jo990989b

  日期：1999.12.1

  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.