rac-(4R,6R)-6-(diethylcarbamoyl)-2,4-dihydroxytetrahydro-2H-pyran-2-carboxylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: rac-(4R,6R)-6-(diethylcarbamoyl)-2,4-dihydroxytetrahydro-2H-pyran-2-carboxylic acid
• 英文别名: (4R,6R)-6-(diethylcarbamoyl)-2,4-dihydroxyoxane-2-carboxylic acid
• 化学式: C₁₁H₁₉NO₆
• 分子量: 261.275
• InChiKey: HSQXYZLWLDEPGD-KQUALDNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N,N,N',N'-tetraethylfumaramide 在 N-acetylneuraminic acid lyase E₁₉₂N mutant 、 水 、 氧气 、 臭氧 、 (S)-N-decyl-N-(pyrrolidin-2-ylmethyl)decan-1-amine 作用下， 以 二氯甲烷 为溶剂， 反应 90.0h， 生成 rac-(4R,6R)-6-(diethylcarbamoyl)-2,4-dihydroxytetrahydro-2H-pyran-2-carboxylic acid 、 rac-(4S,6R)-6-(diethylcarbamoyl)-2,4-dihydroxytetrahydro-2H-pyran-2-carboxylic acid
  参考文献：
  名称：

  Development of an organo- and enzyme-catalysed one-pot, sequential three-component reaction

  摘要：

  A one-pot, three-component process is described which involves both organo- and enzyme-catalysed carbon-carbon bond-forming steps. In the first step, an organocatalyst catalyses the aldol reaction between acetaldehyde and a glyoxylamide. After dilution with additional aqueous buffer, and addition of pyruvate and an aldolase enzyme variant, a second aldol reaction occurs to yield a final product. Crucially, it was possible to develop a reaction in which both the organo- and enzyme-catalysed reactions could be performed in the same aqueous buffer system. The reaction described is the first example of a one-pot, three-component reaction in which the two carbon-carbon bond-forming processes are catalysed using the combination of an organocatalyst and an enzyme. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.010