1-(2-(R)-[6-chloropyridin-3-yloxymethyl]azetedin-1-ylcarboxy)-β-D-glucopyranuronic acid | 1311144-68-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-(R)-[6-chloropyridin-3-yloxymethyl]azetedin-1-ylcarboxy)-β-D-glucopyranuronic acid
• 英文别名: (2S,3S,4S,5R,6S)-6-[(2R)-2-[(6-chloropyridin-3-yl)oxymethyl]azetidine-1-carbonyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 1311144-68-9
• 化学式: C₁₆H₁₉ClN₂O₉
• 分子量: 418.788
• InChiKey: NNFXKNQDJYSAAX-MBUAWJIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  159
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate 在 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 15.75h， 生成 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

文献信息

• Reagents for Stereoselective Preparation of <i>N</i>-Carbamyl β-<scp>d</scp>-Glucuronides
  作者：William H. Bunnelle

  DOI：10.1021/jo200238d

  日期：2011.7.1

  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.