1,9,18-octadecanetriol, 1-tetrahydropyranyl ether, 18-t-butyldimethylsilyl ether | 157189-43-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 1,9,18-octadecanetriol, 1-tetrahydropyranyl ether, 18-t-butyldimethylsilyl ether
• CAS: 157189-43-0
• 化学式: C₂₉H₆₀O₄Si
• 分子量: 500.878
• InChiKey: QBSSNIPKUMLIID-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  1,9,18-octadecanetriol, 1-tetrahydropyranyl ether, 18-t-butyldimethylsilyl ether 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以60%的产率得到1,9,18-octadecanetriol, 1-tetrahydropyranyl ether
  参考文献：
  名称：

  Synthesis and configuration analysis of 9,18- and 10,18-dihydroxystearic acid methyl esters

  摘要：

  The syntheses of 9,18- and 10,18-dihydroxystearic acid methyl esters, which are components of plant cutin, are described. Conversion of the primary alcohol group of these diols to a t-butyldimethylsilyl ether followed by reaction of the residual secondary alcohol group with (S)-(-)-1-(1-naphthyl)ethylisocyanate produces diastereomeric carbamates that are resolved by silica gel high-performance liquid chromatography and whose configurations may be assigned by the H-1-NMR shift differences of the carbomethoxy and silylmethyl signals.

  DOI：

  10.1016/0009-3084(94)90033-7
• 作为产物：
  描述：

  7-octadecyn-1,9,18-triol, 1-tetrahydropyranyl ether, 18-t-butyldimethylsilyl ether 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 1,9,18-octadecanetriol, 1-tetrahydropyranyl ether, 18-t-butyldimethylsilyl ether
  参考文献：
  名称：

  Synthesis and configuration analysis of 9,18- and 10,18-dihydroxystearic acid methyl esters

  摘要：

  The syntheses of 9,18- and 10,18-dihydroxystearic acid methyl esters, which are components of plant cutin, are described. Conversion of the primary alcohol group of these diols to a t-butyldimethylsilyl ether followed by reaction of the residual secondary alcohol group with (S)-(-)-1-(1-naphthyl)ethylisocyanate produces diastereomeric carbamates that are resolved by silica gel high-performance liquid chromatography and whose configurations may be assigned by the H-1-NMR shift differences of the carbomethoxy and silylmethyl signals.

  DOI：

  10.1016/0009-3084(94)90033-7