benzyl 2,3,4-tri-O-benzyl-1-O-(4-nitrophenoxycarbonyl)-β-D-glucopyranuronate | 1311144-66-7

• 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-O-(4-nitrophenoxycarbonyl)-β-D-glucopyranuronate
• 英文别名: 4-Nitrophenoxycarbonyl 2,3,4-tri-O-benzyl-beta-D-glucopyranuronic acid benzyl ester；benzyl (2S,3S,4S,5R,6S)-6-(4-nitrophenoxy)carbonyloxy-3,4,5-tris(phenylmethoxy)oxane-2-carboxylate
• CAS: 1311144-66-7
• 化学式: C₄₁H₃₇NO₁₁
• 分子量: 719.745
• InChiKey: WUGBKECXDPUXLK-BYBAVMQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  53
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  145
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  benzyl 2,3,4-tri-O-benzyl-1-O-(4-nitrophenoxycarbonyl)-β-D-glucopyranuronate 、 2-甲基-3-[[(2S)-吡咯烷-2-基]甲氧基]吡啶 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以89%的产率得到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
• 作为产物：
  描述：

  2,3,4-tri-O-benzyl-D-glucopyranosideuronic acid benzyl ester 、 二(对硝基苯)碳酸酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以72%的产率得到benzyl 2,3,4-tri-O-benzyl-1-O-(4-nitrophenoxycarbonyl)-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

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.