8,10-bis(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-1,3,7,9-tetraoxaspiro[4.5]decan-6-ol | 1196498-70-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8,10-bis(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-1,3,7,9-tetraoxaspiro[4.5]decan-6-ol
• CAS: 1196498-70-0
• 化学式: C₁₈H₃₀O₉
• 分子量: 390.431
• InChiKey: BTFYPZKOFDXQTC-HRMBXJQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.87
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  94.07
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  8,10-bis(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-1,3,7,9-tetraoxaspiro[4.5]decan-6-ol 在 sodium tetrahydroborate 作用下， 以 异丙醇 为溶剂， 生成 (S)-((R)-2,2-dimethyl-1,3-dioxalan-4-yl)((S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol
  参考文献：
  名称：

  Asymmetric Histidine-Catalyzed Cross-Aldol Reactions of Enolizable Aldehydes: Access to Defined Configured Quaternary Stereogenic Centers

  摘要：

  A histidine-catalyzed asymmetric direct cross-aldol reaction of enolizable aldehydes is described. In contrast to proline, histidine is able to clearly differentiate the reactivity of various aldehydes. In addition, this approach provides access to syn-configured B-hydroxyaldehydes. Thus, by application of this new methodology, defined-configuration quaternary stereocenters can be constructed with ease. The utility of this method is demonstrated in several total syntheses of branched-chain carbohydrates.

  DOI：

  10.1021/ja907054y
• 作为产物：
  描述：

  (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 L-组氨酸 作用下， 以 水 为溶剂， 反应 96.0h， 生成 8,10-bis(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-1,3,7,9-tetraoxaspiro[4.5]decan-6-ol
  参考文献：
  名称：

  Asymmetric Histidine-Catalyzed Cross-Aldol Reactions of Enolizable Aldehydes: Access to Defined Configured Quaternary Stereogenic Centers

  摘要：

  A histidine-catalyzed asymmetric direct cross-aldol reaction of enolizable aldehydes is described. In contrast to proline, histidine is able to clearly differentiate the reactivity of various aldehydes. In addition, this approach provides access to syn-configured B-hydroxyaldehydes. Thus, by application of this new methodology, defined-configuration quaternary stereocenters can be constructed with ease. The utility of this method is demonstrated in several total syntheses of branched-chain carbohydrates.

  DOI：

  10.1021/ja907054y