(2S,3R,4S)-2,3:4,5-di-O-(3,3-pentylidene)arabitol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S)-2,3:4,5-di-O-(3,3-pentylidene)arabitol
• 英文别名: [(4S,5R)-5-[(4S)-2,2-diethyl-1,3-dioxolan-4-yl]-2,2-diethyl-1,3-dioxolan-4-yl]methanol
• 化学式: C₁₅H₂₈O₅
• 分子量: 288.384
• InChiKey: QGAKFIZLFWCXMD-RWMBFGLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,3-dimethoxypentane 、 L-(-)-arabitol 在 camphor-10-sulfonic acid 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以80%的产率得到(2S,4S)-1,2:4,5-di-O-(3,3-pentylidene)arabitol
  参考文献：
  名称：

  Efficient Desymmetrization of “Pseudo”-C₂-Symmetric Substrates:  Illustration in the Synthesis of a Disubstituted Butenolide from Arabitol

  摘要：

  A short synthesis of the homochiral disubstituted butenolide 1 is described in four steps from arabitol. The key steps are the selective kinetic protection of arabitol and the cyclization of 11 to form the butenolide ring. This last transformation represents a rare example of a fully stereoselective cyclitive desymmetrization process of a "pseudo"-C-2-symmetric substrate.

  DOI：

  10.1021/jo026696r

文献信息

• Efficient Desymmetrization of “<i>Pseudo</i>”-<i>C</i>₂-Symmetric Substrates:  Illustration in the Synthesis of a Disubstituted Butenolide from Arabitol
  作者：Bruno Linclau、A. James Boydell、Philip J. Clarke、Richard Horan、Claire Jacquet

  DOI：10.1021/jo026696r

  日期：2003.3.1

  A short synthesis of the homochiral disubstituted butenolide 1 is described in four steps from arabitol. The key steps are the selective kinetic protection of arabitol and the cyclization of 11 to form the butenolide ring. This last transformation represents a rare example of a fully stereoselective cyclitive desymmetrization process of a "pseudo"-C-2-symmetric substrate.