(2S,3S,4S,5R,6R)-3,4,5-tris(benzoyloxy)-6-(3-((S)-1-methylpyrrolidin-2-yl)pyridin-1-ium-1-yl)tetrahydro-2H-pyran-2-carboxylate | 1035448-79-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5R,6R)-3,4,5-tris(benzoyloxy)-6-(3-((S)-1-methylpyrrolidin-2-yl)pyridin-1-ium-1-yl)tetrahydro-2H-pyran-2-carboxylate
• CAS: 1035448-79-3
• 化学式: C₃₇H₃₄N₂O₉
• 分子量: 650.685
• InChiKey: DTJPHCVMBWLOLH-DHWPGWDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  48.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  135.38
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzoyl-1-O-methanesulfonyl-α-D-glucopyranuronate 、 烟碱 在 水 作用下， 以 氯仿 、 二氯甲烷 为溶剂， 反应 24.0h， 以62%的产率得到(2S,3S,4S,5R,6R)-3,4,5-tris(benzoyloxy)-6-(3-((S)-1-methylpyrrolidin-2-yl)pyridin-1-ium-1-yl)tetrahydro-2H-pyran-2-carboxylate
  参考文献：
  名称：

  Applicability of Methyl 2,3,4-Tri-O-benzoyl-1-methanesulfonyl-a-D-glucopyranuronate as a Novel Quaternary Glucuronyl Reagent for Tertiary Amines

  摘要：

  Applicability of a methyl 2,3,4-tri-O-benzoyl-1-methanesulfonyl-alpha-D-glucopyranuronate 3 as a novel quaternary glucuronyl reagent was investigated. The reaction of 3 with an aromatic tertiary amines such as pyridine derivatives or imidazole derivatives proceeded to give quaternary N-glucuronides in a moderate yields, but the reaction of 3 with an aliphatic tertiary amine did not occur. In case of the reaction of 3 with nicotine which has aromatic and aliphatic tertiary amines in the molecule, the reaction proceeded selectively on the pyridine ring to give the corresponding N-glucuronide. The present reagent was considered to be useful for the formation of N-quaternary glucuronide from aromatic tertiary amines.

  DOI：

  10.3987/com-07-11289