rac-4-hydroxymethyl-(2R,6R)-2,6-diisopropyl-(1,3)-dioxane-(4S,5S)-4,5-diol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: rac-4-hydroxymethyl-(2R,6R)-2,6-diisopropyl-(1,3)-dioxane-(4S,5S)-4,5-diol
• 英文别名: (2R,4S,5S,6R)-4-(hydroxymethyl)-2,6-di(propan-2-yl)-1,3-dioxane-4,5-diol
• 化学式: C₁₁H₂₂O₅
• 分子量: 234.293
• InChiKey: CMCVOOXJALRNJY-YTWAJWBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,3-二羟基丙酮 、 异丁醛 在 N,N-二异丙基乙胺 作用下， 以92%的产率得到rac-4-hydroxymethyl-(2R,6R)-2,6-diisopropyl-(1,3)-dioxane-(4S,5S)-4,5-diol
  参考文献：
  名称：

  Amine-Catalyzed Direct Aldol Addition

  摘要：

  An efficient organo-catalytic, highly syn-stereoselective method for aldol additions between enolizable aldehydes and hydroxyacetone as well as dihydroxyacetone is disclosed. Reactions proceed in the presence of tertiary amines at room temperature. The aldol adducts can be obtained in good to high yields and with high degrees of syn-diastereoselectivity. This new aldol reaction provides an operationally simple protocol for the stereocontrolled synthesis of carbohydrates

  DOI：

  10.1021/ja071926a

文献信息

• Amine-Catalyzed Direct Aldol Addition
  作者：Morris Markert、Michael Mulzer、Bernd Schetter、Rainer Mahrwald

  DOI：10.1021/ja071926a

  日期：2007.6.13

  An efficient organo-catalytic, highly syn-stereoselective method for aldol additions between enolizable aldehydes and hydroxyacetone as well as dihydroxyacetone is disclosed. Reactions proceed in the presence of tertiary amines at room temperature. The aldol adducts can be obtained in good to high yields and with high degrees of syn-diastereoselectivity. This new aldol reaction provides an operationally simple protocol for the stereocontrolled synthesis of carbohydrates