(2R,3R)-2-((R)-1-hydroxyheptyl)-5-oxotetrahydrofuran-3-carbaldehyde | 1132793-43-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3R)-2-((R)-1-hydroxyheptyl)-5-oxotetrahydrofuran-3-carbaldehyde
• CAS: 1132793-43-1
• 化学式: C₁₂H₂₀O₄
• 分子量: 228.288
• InChiKey: LGKMXCVVFJHWPH-HOSYDEDBSA-N

物化性质

• 沸点：
  398.2±27.0 °C(predicted)
• 密度：
  1.150±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-((R)-1-hydroxyheptyl)-5-oxotetrahydrofuran-3-carbaldehyde 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Chiral vicinal diols as platforms for separable diastereomers in Johnson–Claisen rearrangement: a new short route to (−)-nor-canadensolide, (−)-canadensolide and (−)-sporothriolide

  摘要：

  The chiral vicinal diols prepared by asymmetric dihydroxylation in high enantioselectivities provide an excellent platform for separable diastereomers in the Johnson-Claisen rearrangement. The separated syn-diastereomers were converted into the advanced gamma-(lactone-lactol) intermediates (in six steps, 26-27% overall yields) for the synthesis of (-)-nor-canadensoiide, (-)-canadensolide and (-)-sporothriolide. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.12.084
• 作为产物：
  描述：

  (4S,5R)-4-vinyl-5-[(R)-1-hydroxyheptyl]-4,5-dihydro-2(3H)-furanone 在 臭氧 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以95%的产率得到(2R,3R)-2-((R)-1-hydroxyheptyl)-5-oxotetrahydrofuran-3-carbaldehyde
  参考文献：
  名称：

  Synthesis of β,γ-disubstituted-γ-lactones through a Johnson–Claisen rearrangement: a short route to xylobovide, nor-canadensolide, canadensolide, sporothriolide and santolinolide

  摘要：

  The Johnson-Claisen rearrangement of allyl alcohols with chiral vicinal diol functionality was employed to access chiral beta,gamma-disubstituted-gamma-lactones in high enantio- and diastereoselectivity. These were efficiently converted into nor-canadensolide, the advanced gamma-(lactone-lactol) intermediate for xylobovide, canadensolide and sporothriolide and the lactone moiety of the santolinolides. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.11.018