methyl 2,3,4-tri-O-benzoyl-1-O-methanesulfonyl-α-D-glucopyranuronate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzoyl-1-O-methanesulfonyl-α-D-glucopyranuronate
• 英文别名: methyl 2,3,4-tri-O-benzoyl-1-methanesulfonyl-α-D-glucopyranuronate；alpha-d-Glucopyranuronic acid methyl ester 2,3,4-tribenzoate 1-methanesulfonate；methyl (2S,3S,4S,5R,6R)-3,4,5-tribenzoyloxy-6-methylsulfonyloxyoxane-2-carboxylate
• 化学式: C₂₉H₂₆O₁₂S
• 分子量: 598.584
• InChiKey: KYVGRCQMYCSHFD-LDJGUTQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  166
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  甲烷磺酸 、 methyl 1,2,3,4-tetra-O-benzoyl-β-D-glucopyranuronate 以 二氯甲烷 为溶剂， 反应 0.75h， 以49%的产率得到methyl 2,3,4-tri-O-benzoyl-1-O-methanesulfonyl-α-D-glucopyranuronate
  参考文献：
  名称：

  Synthesis of the Metabolites of 4-(2-Methyl-1H-imidazol-1-yl)-2,2-diphenylbutanamide (KRP-197/ONO-8025)

  摘要：

  我们合成了4-(2-甲基-1H-咪唑-1-基)-2,2-二苯基丁酰胺[KRP-197/ONO-8025, 1]这一尿失禁治疗药物的六种假定代谢物（2—7），以确认这些代谢物的结构。代谢物（2）通过化合物（1）与甲基2,3,4-三-O-苯甲酰基-1-甲磺酰基-α-D-吡喃葡萄糖醛酸的葡萄糖醛酸化反应合成。代谢物（3）通过3-(叔丁氧羰基)-2-甲基-1,3-咪唑烷-4,5-二酮合成。代谢物（4—7）分别通过4-氨基-2-二苯基丁酰胺合成。通过合成标准化合物，确定了人体内代谢物（2—7）的结构。

  DOI：

  10.1248/cpb.55.1039

文献信息

• Synthesis of the Metabolites of 4-(2-Methyl-1H-imidazol-1-yl)-2,2-diphenylbutanamide (KRP-197/ONO-8025)
  作者：Ichiro Araya、Takeshi Tsubuki、Tatsuhiro Saito、Makoto Numata、Hiroyuki Akita

  DOI：10.1248/cpb.55.1039

  日期：——

  We synthesized the six presumed metabolites (2—7) of 4-(2-methyl-1H-imidazol-1-yl)-2,2-diphenylbutanamide [KRP-197/ONO-8025, 1], a urinary incontinence therapeutic agent, in order to confirm the structures of the metabolites. Metabolite (2) was synthesized via glucuronidaion of compound (1) and methyl 2,3,4-tri-O-benzoyl-1-methanesulfonyl-α-D-glucopyranuronate. Metabolite (3) was synthesized via 3-(tert-butoxycarbonyl)-2-methyl-1,3-imidazolidine-4,5-dione. Metabolites (4—7) were synthesized via 4-amino-2-diphenylbutanamide, respectively. The structures of the metabolites (2—7) in humans were identified by means of synthesis of the authentic compounds.

  我们合成了4-(2-甲基-1H-咪唑-1-基)-2,2-二苯基丁酰胺[KRP-197/ONO-8025, 1]这一尿失禁治疗药物的六种假定代谢物（2—7），以确认这些代谢物的结构。代谢物（2）通过化合物（1）与甲基2,3,4-三-O-苯甲酰基-1-甲磺酰基-α-D-吡喃葡萄糖醛酸的葡萄糖醛酸化反应合成。代谢物（3）通过3-(叔丁氧羰基)-2-甲基-1,3-咪唑烷-4,5-二酮合成。代谢物（4—7）分别通过4-氨基-2-二苯基丁酰胺合成。通过合成标准化合物，确定了人体内代谢物（2—7）的结构。
• Applicability of Methyl 2,3,4-Tri-O-benzoyl-1-methanesulfonyl-a-D-glucopyranuronate as a Novel Quaternary Glucuronyl Reagent for Tertiary Amines
  作者：Ichiro Araya、Hiroyuki Akita

  DOI：10.3987/com-07-11289

  日期：——

  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.