β-2-C-(hydroxymethyl)-D-lyxose | 1196498-71-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-2-C-(hydroxymethyl)-D-lyxose
• 英文别名: (2R,3S,4S,5R)-3-(hydroxymethyl)oxane-2,3,4,5-tetrol
• CAS: 1196498-71-1
• 化学式: C₆H₁₂O₆
• 分子量: 180.158
• InChiKey: LPZIZDWZKIXVRZ-MOJAZDJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 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 DOWEX-50WX₂ 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 12.0h， 生成 β-2-C-(hydroxymethyl)-D-lyxose 、 α-2-C-(hydroxymethyl)-D-lyxose
  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.