(2R,3S,4aR,6S,7R,9aS)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-(2-hydroxy-ethyl)-octahydro-1,5-dioxa-benzocyclohepten-7-ol | 208454-47-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4aR,6S,7R,9aS)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-(2-hydroxy-ethyl)-octahydro-1,5-dioxa-benzocyclohepten-7-ol
• 英文别名: (2R,3S,4aR,6S,7R,9aS)-3-[tert-butyl(diphenyl)silyl]oxy-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-6-(2-hydroxyethyl)-3,4,4a,6,7,8,9,9a-octahydro-2H-pyrano[3,2-b]oxepin-7-ol
• CAS: 208454-47-1
• 化学式: C₄₄H₅₈O₆Si₂
• 分子量: 739.112
• InChiKey: NHTGNLYMORPRAQ-ABXWMRQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.96
• 重原子数：
  52
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S,4aR,6S,7R,9aS)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-(2-hydroxy-ethyl)-octahydro-1,5-dioxa-benzocyclohepten-7-ol 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 、 偶氮二异丁腈 、 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 、 甲苯 、 乙腈 、 叔丁醇 、 苯 为溶剂， 反应 29.5h， 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
• 作为产物：
  描述：

  (2R,3S,4aR,6S,7R,9aS)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-vinyl-octahydro-1,5-dioxa-benzocyclohepten-7-ol 在 9-硼双环[3.3.1]壬烷 、 双氧水 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 生成 (2R,3S,4aR,6S,7R,9aS)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-(2-hydroxy-ethyl)-octahydro-1,5-dioxa-benzocyclohepten-7-ol
  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.