ethyl 3-(N-2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl-carbamoyl)-(E)-propenoate | 896730-83-9

• 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: ethyl 3-(N-2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl-carbamoyl)-(E)-propenoate
• CAS: 896730-83-9
• 化学式: C₂₀H₂₇NO₁₂
• 分子量: 473.434
• InChiKey: OWPYRARMYZFVLI-CQGZIQSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.69
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  169.83
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-(N-2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl-carbamoyl)-(E)-propenoate 、 甲醇 在 sodium methylate 作用下， 以86%的产率得到methyl 3-(N-β-D-glucopyranosyl-carbamoyl)-(E)-propenoate
  参考文献：
  名称：

  Synthesis of N-(β-d-glucopyranosyl) monoamides of dicarboxylic acids as potential inhibitors of glycogen phosphorylase

  摘要：

  O-Peracetylated N-(beta-D-glucopyranosyl)imino trimethylphosphorane obtained in situ from 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl azide and PMe3 was reacted with saturated and unsaturated aliphatic and aromatic dicarboxylic acids, or their anhydrides. or monoesters to give the corresponding N-(beta-D-glucopyranosyl) monoamides of dicarboxylic acids or derivatives. The acetyl protecting groups were removed according to the Zemplen protocol to give a series of compounds which showed moderate inhibitory effects against rabbit muscle glycogen phosphorylase b. The best inhibitor was 3-(N-beta-D-glucopyranosyl-carbamoy)propanoic acid (7) with K-i = 20 mu M. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.002
• 作为产物：
  描述：

  1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 以 二氯甲烷 为溶剂， 生成 ethyl 3-(N-2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl-carbamoyl)-(E)-propenoate
  参考文献：
  名称：

  Synthesis of N-(β-d-glucopyranosyl) monoamides of dicarboxylic acids as potential inhibitors of glycogen phosphorylase

  摘要：

  O-Peracetylated N-(beta-D-glucopyranosyl)imino trimethylphosphorane obtained in situ from 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl azide and PMe3 was reacted with saturated and unsaturated aliphatic and aromatic dicarboxylic acids, or their anhydrides. or monoesters to give the corresponding N-(beta-D-glucopyranosyl) monoamides of dicarboxylic acids or derivatives. The acetyl protecting groups were removed according to the Zemplen protocol to give a series of compounds which showed moderate inhibitory effects against rabbit muscle glycogen phosphorylase b. The best inhibitor was 3-(N-beta-D-glucopyranosyl-carbamoy)propanoic acid (7) with K-i = 20 mu M. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.002