methyl {[2-(chloromethyl)-4-nitrophenyl] 2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate | 353249-43-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl {[2-(chloromethyl)-4-nitrophenyl] 2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate
• 英文别名: methyl (2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[2-(chloromethyl)-4-nitrophenoxy]oxane-2-carboxylate
• CAS: 353249-43-1
• 化学式: C₂₀H₂₂ClNO₁₂
• 分子量: 503.847
• InChiKey: FNHRBOQAOMHSLC-KVIJGQROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  170
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl {[2-(chloromethyl)-4-nitrophenyl] 2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate 在 sodium hydroxide 、 sodium methylate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 4.25h， 生成 [2-(chloromethyl)-4-nitrophenyl] β-D-glucopyranosiduronic acid
  参考文献：
  名称：

  2-Nitro and 4-nitro-quinone-methides are not irreversible inhibitors of bovine β-glucuronidase

  摘要：

  4-Benzylamino-(and 4-chloromethyl)-2-nitro-beta -D-glucuronides (4, 10) and their 2-substituted-4-nitro regioisomers (7, 13) were prepared by glycosidation of the 3-nitro-4-hydroxy- and the 2-hydroxy-5-nitro-benzylic alcohol, respectively, with a glucuronyl donor. Carbonate activation followed by reaction with benzylamine or methanesulfonyl chloride afforded, after complete deprotection, the target molecules 4, 7, 10 and 13. These compounds have been synthesized to determine whether these molecules are (or not) glucuronidase inhibitors. After incubation with bovine liver beta -glucuronidase, none of the cleavage products (the titled quinone-methides) showed to be irreversible inhibitors of this enzyme. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(01)00083-0
• 作为产物：
  描述：

  methyl {[2-(hydroxymethyl)-4-nitrophenyl] 2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate 在 甲基磺酰氯 作用下， 以 吡啶 为溶剂， 反应 3.0h， 以60%的产率得到methyl {[2-(chloromethyl)-4-nitrophenyl] 2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate
  参考文献：
  名称：

  2-Nitro and 4-nitro-quinone-methides are not irreversible inhibitors of bovine β-glucuronidase

  摘要：

  4-Benzylamino-(and 4-chloromethyl)-2-nitro-beta -D-glucuronides (4, 10) and their 2-substituted-4-nitro regioisomers (7, 13) were prepared by glycosidation of the 3-nitro-4-hydroxy- and the 2-hydroxy-5-nitro-benzylic alcohol, respectively, with a glucuronyl donor. Carbonate activation followed by reaction with benzylamine or methanesulfonyl chloride afforded, after complete deprotection, the target molecules 4, 7, 10 and 13. These compounds have been synthesized to determine whether these molecules are (or not) glucuronidase inhibitors. After incubation with bovine liver beta -glucuronidase, none of the cleavage products (the titled quinone-methides) showed to be irreversible inhibitors of this enzyme. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(01)00083-0