methyl 2,3,4-tri-O-acetyl-1-(2-(R)-[6-chloropyridin-3-yloxymethyl]azetedin-1-ylcarboxy)-β-D-glucopyranuronate | 1311144-67-8

• 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-acetyl-1-(2-(R)-[6-chloropyridin-3-yloxymethyl]azetedin-1-ylcarboxy)-β-D-glucopyranuronate
• 英文别名: [(2S,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-methoxycarbonyloxan-2-yl] (2R)-2-[(6-chloropyridin-3-yl)oxymethyl]azetidine-1-carboxylate
• CAS: 1311144-67-8
• 化学式: C₂₃H₂₇ClN₂O₁₂
• 分子量: 558.927
• InChiKey: HKLNJJSUJFVJNP-DARYBUAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  166
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-acetyl-1-(2-(R)-[6-chloropyridin-3-yloxymethyl]azetedin-1-ylcarboxy)-β-D-glucopyranuronate 在 N,N-二异丙基乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 14.0h， 以67%的产率得到1-(2-(R)-[6-chloropyridin-3-yloxymethyl]azetedin-1-ylcarboxy)-β-D-glucopyranuronic acid
  参考文献：
  名称：

  Reagents for Stereoselective Preparation of N-Carbamyl β-d-Glucuronides

  摘要：

  Carbamyl glucuronidation is an increasingly well-recognized route of metabolism for secondary amine drugs. Proper characterization of these metabolites requires the synthesis of authentic standards. beta-Protected glucuronyl beta-nitrophenyl carbonates can be prepared with high selectivity for the beta-configuration at the anomeric center and efficiently transfer the beta-glucuronylcarbonyl group to secondary amines, constituting an effective and versatile method for preparation of these metabolites.

  DOI：

  10.1021/jo200238d
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.75h， 生成 methyl 2,3,4-tri-O-acetyl-1-(2-(R)-[6-chloropyridin-3-yloxymethyl]azetedin-1-ylcarboxy)-β-D-glucopyranuronate
  参考文献：
  名称：

  Reagents for Stereoselective Preparation of N-Carbamyl β-d-Glucuronides

  摘要：

  Carbamyl glucuronidation is an increasingly well-recognized route of metabolism for secondary amine drugs. Proper characterization of these metabolites requires the synthesis of authentic standards. beta-Protected glucuronyl beta-nitrophenyl carbonates can be prepared with high selectivity for the beta-configuration at the anomeric center and efficiently transfer the beta-glucuronylcarbonyl group to secondary amines, constituting an effective and versatile method for preparation of these metabolites.

  DOI：

  10.1021/jo200238d