(S)-((R)-2,2-dimethyl-1,3-dioxalan-4-yl)((S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol | 1196499-08-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-((R)-2,2-dimethyl-1,3-dioxalan-4-yl)((S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol
• 英文别名: (S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-[(4S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol
• CAS: 1196499-08-7
• 化学式: C₁₂H₂₂O₆
• 分子量: 262.303
• InChiKey: MGJMYAGNAQVELD-PTRXPTGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-((R)-2,2-dimethyl-1,3-dioxalan-4-yl)((S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成
  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：

  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