(2R,3R)-3-hydroxy-4,4-dimethoxy-2-methyl-2-phenylbutyraldehyde | 1196498-62-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R)-3-hydroxy-4,4-dimethoxy-2-methyl-2-phenylbutyraldehyde
• 英文别名: (2R,3R)-3-hydroxy-4,4-dimethoxy-2-methyl-2-phenylbutanal
• CAS: 1196498-62-0
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: VLQMCWYYJTYGCT-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-hydroxy-4,4-dimethoxy-2-methyl-2-phenylbutyraldehyde 在 sodium tetrahydroborate 作用下， 以 异丙醇 为溶剂， 生成 syn-(2S,3R)-2-methyl-2-phenyl-4,4-dimethoxy-1,3-butandiol
  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：

  乙二醛-1,1-二甲基乙缩醛溶液 、 2-苯基丙醛 在 L-组氨酸 作用下， 以 水 为溶剂， 生成 (2R,3R)-3-hydroxy-4,4-dimethoxy-2-methyl-2-phenylbutyraldehyde 、 (2S,3S)-3-hydroxy-4,4-dimethoxy-2-methyl-2-phenylbutyraldehyde 、 (2S,3R)-3-hydroxy-4,4-dimethoxy-2-methyl-2-phenylbutyraldehyde
  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

文献信息

• Asymmetric Histidine-Catalyzed Cross-Aldol Reactions of Enolizable Aldehydes: Access to Defined Configured Quaternary Stereogenic Centers
  作者：Morris Markert、Ulf Scheffler、Rainer Mahrwald

  DOI：10.1021/ja907054y

  日期：2009.11.25

  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.