(4R,5R,6R)-6-dipropylcarbamoyl-2-oxo-4,5,6-trihydroxy-hexanoic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R,6R)-6-dipropylcarbamoyl-2-oxo-4,5,6-trihydroxy-hexanoic acid
• 英文别名: (4R,5R,6R)-6-(dipropylcarbamoyl)-2,4,5-trihydroxyoxane-2-carboxylic acid
• 化学式: C₁₃H₂₃NO₇
• 分子量: 305.328
• InChiKey: YOLAUIMRJUSMCJ-PNFNOFIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  128
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  D-erythronolactone acetonide 在 indium 、 barium dihydroxide 、 草酰氯 、 臭氧 、 二甲基亚砜 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 (4R,5R,6R)-6-dipropylcarbamoyl-2-oxo-4,5,6-trihydroxy-hexanoic acid
  参考文献：
  名称：

  创建用于平行合成唾液酸模拟物的量身定制的醛缩酶。

  摘要：

  DOI：

  10.1002/anie.200462733

文献信息

• Development of an organo- and enzyme-catalysed one-pot, sequential three-component reaction
  作者：Angela Kinnell、Thomas Harman、Matilda Bingham、Alan Berry、Adam Nelson

  DOI：10.1016/j.tet.2012.02.010

  日期：2012.9

  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.
• Creation of a Tailored Aldolase for the Parallel Synthesis of Sialic Acid Mimetics
  作者：Thomas Woodhall、Gavin Williams、Alan Berry、Adam Nelson

  DOI：10.1002/anie.200462733

  日期：2005.3.29