N-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-glutarimide | 896730-78-2

• 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: N-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-glutarimide
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(2,6-dioxopiperidin-1-yl)oxan-2-yl]methyl acetate
• CAS: 896730-78-2
• 化学式: C₁₉H₂₅NO₁₁
• 分子量: 443.408
• InChiKey: NGSDXMIKLDHEMS-LQDZTQBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  152
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  N-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-glutarimide 、 甲醇 在 sodium methylate 作用下， 以75%的产率得到N-pentanedioic acid-β-D-glucopyranosylamide methyl ester
  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 N-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-glutarimide
  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