2,4-dimethyl-2,4,6,7-tetradeoxy-D-allo-heptose | 170421-32-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2,4-dimethyl-2,4,6,7-tetradeoxy-D-allo-heptose
• 英文别名: 2H-Pyran-2,4-diol, 6-ethyltetrahydro-3,5-dimethyl-, [2S-(2I+/-,3I+/-,4I+/-,5I+/-,6I(2))]-；(2S,3R,4R,5S,6R)-6-ethyl-3,5-dimethyloxane-2,4-diol
• CAS: 170421-32-6
• 化学式: C₉H₁₈O₃
• 分子量: 174.24
• InChiKey: DZUQYEPFSRMAAG-OKNNCHMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 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：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  丙醛 在 三乙醇胺 、 乙二胺四乙酸 作用下， 反应 336.0h， 生成 2,4-dimethyl-2,4,6,7-tetradeoxy-D-allo-heptose 、 2,4-dimethyl-2,4,6,7-tetradeoxy-D-allo-heptose
  参考文献：
  名称：

  Sequential Three- and Four-Substrate Aldol Reactions Catalyzed by Aldolases

  摘要：

  This paper describes a useful synthetic strategy based on sequential enzyme-catalyzed aldol addition reactions. The aldol reaction of an acceptor aldehyde with acetaldehyde, catalyzed by 2-deoxyribose-5-phosphate aldolase (DERA, EC 4.1.2.4), gives a new aldehyde, which subsequently reacts with a second donor substrate, catalyzed by DERA or another aldolase. This sequential aldol reaction proceeds because of the formation of a stable cyclic hemiacetal or hemiketal product. In this way several 6-substituted 2,4,6-trideoxyhexoses have been stereoselectively synthesized via a one-pot double DERA-catalyzed reaction. DERA coupled with fructose-1,6-diphosphate aldolase from rabbit muscle (RAMA, EC 4.1.2.13) in a one-pot reaction gave a variety of 5-deoxyheptuloses, however not in 100% stereoselectivity. The sequential aldol reactions with four substrates were accomplished by coupling DERA with N-acetylneuraminic acid aldolase (NeuAc aldolase, EC 4.1.3.3) to give several nine-carbon sialic acid-type sugar derivatives.

  DOI：

  10.1021/ja00134a001

文献信息

• Sequential Three- and Four-Substrate Aldol Reactions Catalyzed by Aldolases
  作者：Harrie J. M. Gijsen、Chi-Huey Wong

  DOI：10.1021/ja00134a001

  日期：1995.7

  This paper describes a useful synthetic strategy based on sequential enzyme-catalyzed aldol addition reactions. The aldol reaction of an acceptor aldehyde with acetaldehyde, catalyzed by 2-deoxyribose-5-phosphate aldolase (DERA, EC 4.1.2.4), gives a new aldehyde, which subsequently reacts with a second donor substrate, catalyzed by DERA or another aldolase. This sequential aldol reaction proceeds because of the formation of a stable cyclic hemiacetal or hemiketal product. In this way several 6-substituted 2,4,6-trideoxyhexoses have been stereoselectively synthesized via a one-pot double DERA-catalyzed reaction. DERA coupled with fructose-1,6-diphosphate aldolase from rabbit muscle (RAMA, EC 4.1.2.13) in a one-pot reaction gave a variety of 5-deoxyheptuloses, however not in 100% stereoselectivity. The sequential aldol reactions with four substrates were accomplished by coupling DERA with N-acetylneuraminic acid aldolase (NeuAc aldolase, EC 4.1.3.3) to give several nine-carbon sialic acid-type sugar derivatives.