[(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 | 208454-44-8

• 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-formyl-2,6,11,18,23-pentaoxapentacyclo[15.9.0.03,12.05,10.019,24]hexacosan-15-yl] acetate
• CAS: 208454-44-8
• 化学式: C₂₈H₄₄O₈S₂
• 分子量: 572.785
• InChiKey: KXQQLFGQGGJCLY-GRBCIZHKSA-N

物化性质

• 沸点：
  688.2±55.0 °C(predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  140
• 氢给体数：
  0
• 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-formyl-2,6,11,18,23-pentaoxapentacyclo[15.9.0.03,12.05,10.019,24]hexacosan-15-yl] acetate 、 在 正丁基锂 、 六甲基磷酰三胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以210.6 mg的产率得到[(1R,3S,5R,10S,12R,15S,17S,19R,22R,24S)-22-[(Z)-3-[(1R,3S,4'S,5R,6S,8R,9S,10S,11S,13R,14S,15S)-5-[tert-butyl(dimethyl)silyl]oxy-9,14,15-trimethyl-4',10-bis(phenylmethoxy)spiro[2,7,12-trioxatricyclo[9.4.0.03,8]pentadecane-13,2'-oxolane]-6-yl]prop-1-enyl]-21,21-bis(ethylsulfanyl)-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：

  (2R,3S,4aR,5aS,9R,10aR,12aS)-9-((2R,3S)-3-Allyloxy-tetrahydro-pyran-2-ylmethyl)-3-(tert-butyl-diphenyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-decahydro-1,5,8,10-tetraoxa-benzo[b]heptalene 在 咪唑 、 2,6-二甲基吡啶 、 lead(IV) acetate 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 四氧化锇 、 samarium diiodide 、 草酰氯 、 三乙基硼 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 仲丁基锂 、 三正丁基氢锡 、 三氧化硫吡啶 、 四氯化钛 、 二甲基亚砜 、 N-甲基吗啉氧化物 、 三乙胺 、 三苯基膦 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 、 叔丁醇 、 苯 为溶剂， 反应 32.0h， 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