Acetic acid 3-((4aR,6S,7R,8aS)-7-hydroxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-propyl ester | 208454-68-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid 3-((4aR,6S,7R,8aS)-7-hydroxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-propyl ester
• 英文别名: 3-[(4aR,6S,7R,8aS)-7-hydroxy-2,2-dimethyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]propyl acetate
• CAS: 208454-68-6
• 化学式: C₁₄H₂₄O₆
• 分子量: 288.341
• InChiKey: WMVZZAWJSOGCKG-MROQNXINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Acetic acid 3-((4aR,6S,7R,8aS)-7-hydroxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-propyl ester 在 咪唑 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 Acetic acid 3-[(2S,3R,5S,6R)-3-allyloxy-5-(tert-butyl-diphenyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-propyl ester
  参考文献：
  名称：

  Synthetic Studies on Ciguatoxin: A Convergent Strategy for Construction of the F-M Ring Framework

  摘要：

  Exceptional neurotoxicity is associated with ciguatoxin. The ciguatoxin mimic 1, which contains the F-M framework of the natural product, has been prepared through a convergent synthesis. The two key steps were a Lewis acid mediated intramolecular reaction of a γ-alkoxyallylsilane with an acetal group and an SmI2 -mediated intramolecular Reformatsky reaction that permitted construction of the annelated hexahydrooxonin ring system.

  DOI：

  10.1002/(sici)1521-3773(19980420)37:7<965::aid-anie965>3.0.co;2-p
• 作为产物：
  描述：

  3-(2',4',6'-tri-O-Benzyl-3'-deoxy-β-D-glucopyranosyl)-1-propanol 在 palladium dihydroxide 4-二甲氨基吡啶 、 氢气 、 4-甲基苯磺酸吡啶 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 Acetic acid 3-((4aR,6S,7R,8aS)-7-hydroxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-propyl ester
  参考文献：
  名称：

  Synthetic Studies on Ciguatoxin: A Convergent Strategy for Construction of the F-M Ring Framework

  摘要：

  Exceptional neurotoxicity is associated with ciguatoxin. The ciguatoxin mimic 1, which contains the F-M framework of the natural product, has been prepared through a convergent synthesis. The two key steps were a Lewis acid mediated intramolecular reaction of a γ-alkoxyallylsilane with an acetal group and an SmI2 -mediated intramolecular Reformatsky reaction that permitted construction of the annelated hexahydrooxonin ring system.

  DOI：

  10.1002/(sici)1521-3773(19980420)37:7<965::aid-anie965>3.0.co;2-p