methyl 5-azido-3,6-di-O-benzyl-5-deoxy-2-O-methanesulfonyl-L-idonamide | 1591782-85-2

• 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 5-azido-3,6-di-O-benzyl-5-deoxy-2-O-methanesulfonyl-L-idonamide
• CAS: 1591782-85-2
• 化学式: C₂₂H₂₈N₄O₇S
• 分子量: 492.553
• InChiKey: XBGNXXXXZNKKJT-WOZUAGRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 重原子数：
  34.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  159.92
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  5-azido-3,6-di-O-benzyl-5-deoxy-L-gulono-1,4-lactone 在 吡啶 、 甲胺 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 2.0h， 生成 methyl 5-azido-3,6-di-O-benzyl-5-deoxy-2-O-methanesulfonyl-L-idonamide 、 methyl 5-azido-3,6-di-O-benzyl-5-deoxy-2-O-methanesulfonyl-L-gulonamide
  参考文献：
  名称：

  Nine of 16 Stereoisomeric Polyhydroxylated Proline Amides Are Potent β-N-Acetylhexosaminidase Inhibitors

  摘要：

  All 16 stereoisomeric N-methyl 5-(hydroxymethyl)-3,4-dihydroxyproline amides have been synthesized from lactones accessible from the enantiomers of glucuronolactone. Nine stereoisomers, including all eight with a (3R)-hydroxyl configuration, are low to submicromolar inhibitors of beta-N-acetylhexosaminidases. A structural correlation between the proline amides is found with the ADMDP-acetamide analogues bearing an acetamidomethylpyrrolidine motif. The proline amides are generally more potent than their ADMDP-acetamide equivalents. beta-N-Acetylhexosaminidase inhibition by an azetidine ADMDP-acetamide analogue is compared to an azetidine carboxylic acid amide. None of the amides are good alpha-N-acetylgalactosaminidase inhibitors.

  DOI：

  10.1021/jo500157p