methyl 2-O-benzoyl-3,4,6-trideoxy-6-azido-α-D-threo-hex-3-enopyranoside | 651302-49-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-O-benzoyl-3,4,6-trideoxy-6-azido-α-D-threo-hex-3-enopyranoside
• CAS: 651302-49-7
• 化学式: C₁₄H₁₅N₃O₄
• 分子量: 289.291
• InChiKey: HYFNCRJDIJEWDD-OBJOEFQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  93.52
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 2-O-benzoyl-3,4,6-trideoxy-6-azido-α-D-threo-hex-3-enopyranoside 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.5h， 以83%的产率得到methyl 3,4,6-trideoxy-6-amino-α-D-threo-hex-3-enopyranoside
  参考文献：
  名称：

  Synthesis of Unsaturated Aminopyranosides as Possible Transition State Mimics for Glycosidases

  摘要：

  Four unsaturated aminopyranosides have been prepared as possible transition-state mimics targeted towards carbohydrate processing enzymes. The conformations of the protonated aminosugars have been investigated by molecular modelling and their ability to inhibit alpha- and beta-glucosidases and an a-mannosidase have been probed. Two targets proved moderate inhibitors of alpha-glucosidases from Brewer's yeast and Bacillus stearothennophilus.

  DOI：

  10.1081/car-120026469
• 作为产物：
  描述：

  (2S,3R,6S)-6-(hydroxymethyl)-2-methoxy-3,6-dihydro-2H-pyran-3-ol 在 sodium azide 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 methyl 2-O-benzoyl-3,4,6-trideoxy-6-azido-α-D-threo-hex-3-enopyranoside
  参考文献：
  名称：

  Synthesis of Unsaturated Aminopyranosides as Possible Transition State Mimics for Glycosidases

  摘要：

  Four unsaturated aminopyranosides have been prepared as possible transition-state mimics targeted towards carbohydrate processing enzymes. The conformations of the protonated aminosugars have been investigated by molecular modelling and their ability to inhibit alpha- and beta-glucosidases and an a-mannosidase have been probed. Two targets proved moderate inhibitors of alpha-glucosidases from Brewer's yeast and Bacillus stearothennophilus.

  DOI：

  10.1081/car-120026469