benzyl 2,3,4-tri-O-benzyl-1-(2-(S)-[2-methylpyridin-3-yloxymethyl]pyrrolidin-1-ylcarboxy)-β-D-glucopyranuronate | 1311144-70-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2,3,4-tri-O-benzyl-1-(2-(S)-[2-methylpyridin-3-yloxymethyl]pyrrolidin-1-ylcarboxy)-β-D-glucopyranuronate
• 英文别名: [(2S,3R,4S,5S,6S)-3,4,5-tris(phenylmethoxy)-6-phenylmethoxycarbonyloxan-2-yl] (2S)-2-[(2-methylpyridin-3-yl)oxymethyl]pyrrolidine-1-carboxylate
• CAS: 1311144-70-3
• 化学式: C₄₆H₄₈N₂O₉
• 分子量: 772.895
• InChiKey: LFCPLEQTCIDSKA-WHWCMPSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  57
• 可旋转键数：
  18
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  benzyl 2,3,4-tri-O-benzyl-1-(2-(S)-[2-methylpyridin-3-yloxymethyl]pyrrolidin-1-ylcarboxy)-β-D-glucopyranuronate 在 20 % Pd(OH)2/C 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 46.0h， 以98%的产率得到1-(2-(S)-[2-methylpyridin-3-yloxymethyl]pyrrolidin-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：

  2,3,4-tri-O-benzyl-D-glucopyranosideuronic acid benzyl ester 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 benzyl 2,3,4-tri-O-benzyl-1-(2-(S)-[2-methylpyridin-3-yloxymethyl]pyrrolidin-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