2-(2-azidoethoxy)ethyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside | 203251-76-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(2-azidoethoxy)ethyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside
• CAS: 203251-76-7
• 化学式: C₃₈H₃₅N₃O₁₁
• 分子量: 709.709
• InChiKey: NUWXNXISJZOXPK-RMVWMXAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.59
• 重原子数：
  52.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  181.65
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2-(2-azidoethoxy)ethyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside 在 sodium hydroxide 、 sodium methylate 、 四丁基硫酸氢铵 、 zinc(II) chloride 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 72.5h， 生成
  参考文献：
  名称：

  Synthesis of Carbohydrate Haptens to be Used for Generation of Catalytic Antibodies

  摘要：

  The glycoside 2-(2-azidoethoxy)ethyl 2-O-benzyl-4,6-O-benzylidene-beta-D-glucopyranoside was prepared and then reacted, first with methyl phosphonyl dichloride, then with dimethylaminoethanol, to give the methylphosphonyl diester 9. N-Methylation of 9 with methyl iodide and subsequent catalytic hydrogenation gave the methylphosphonyl diester 11. The corresponding phenylphosphonyl diester 14 was also prepared in a similar way. The phosphonyl diesters 11 and 14 are analogs of the transition states for 3-O-acetylation and 3-O-benzoylation of P-D glucopyranose derivatives with acetyl-and benzoylcholine, respectively. They will be used for generation of catalytic antibodies.

  DOI：

  10.1080/07328309808005774
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzoylglucosyl bromide 、 2-(2-叠氮乙氧基)乙醇 在 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以76%的产率得到2-(2-azidoethoxy)ethyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Carbohydrate Haptens to be Used for Generation of Catalytic Antibodies

  摘要：

  The glycoside 2-(2-azidoethoxy)ethyl 2-O-benzyl-4,6-O-benzylidene-beta-D-glucopyranoside was prepared and then reacted, first with methyl phosphonyl dichloride, then with dimethylaminoethanol, to give the methylphosphonyl diester 9. N-Methylation of 9 with methyl iodide and subsequent catalytic hydrogenation gave the methylphosphonyl diester 11. The corresponding phenylphosphonyl diester 14 was also prepared in a similar way. The phosphonyl diesters 11 and 14 are analogs of the transition states for 3-O-acetylation and 3-O-benzoylation of P-D glucopyranose derivatives with acetyl-and benzoylcholine, respectively. They will be used for generation of catalytic antibodies.

  DOI：

  10.1080/07328309808005774