methyl 7-azido-5,7-dideoxy-D-lyxo-heptuloside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 7-azido-5,7-dideoxy-D-lyxo-heptuloside
• 英文别名: (2S,3S,4S,6S)-6-(azidomethyl)-2-(hydroxymethyl)-2-methoxyoxane-3,4-diol
• 化学式: C₈H₁₅N₃O₅
• 分子量: 233.224
• InChiKey: DLAHEGKFPXKFGI-XAMCCFCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  93.5
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  甲醇 、 6-Azidomethyl-2-hydroxymethyl-tetrahydro-pyran-2,3,4-triol 在 Dowex 50(H⁺) 作用下， 生成 methyl 7-azido-5,7-dideoxy-L-lyxo-heptuloside 、 methyl 7-azido-5,7-dideoxy-D-arabino-heptuloside 、 methyl 7-azido-5,7-dideoxy-D-lyxo-heptuloside
  参考文献：
  名称：

  Sequential One-Pot Aldol Reactions Catalyzed by 2-Deoxyribose-5-phosphate Aldolase and Fructose-1,6-diphosphate Aldolase

  摘要：

  DOI：

  10.1021/ja00115a038

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.
• Sequential One-Pot Aldol Reactions Catalyzed by 2-Deoxyribose-5-phosphate Aldolase and Fructose-1,6-diphosphate Aldolase
  作者：Harrie J. M. Gijsen、Chi-Huey Wong

  DOI：10.1021/ja00115a038

  日期：1995.3