N-pentanedioic acid-β-D-glucopyranosylamide methyl ester

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-pentanedioic acid-β-D-glucopyranosylamide methyl ester
• 英文别名: methyl 4-(N-β-D-glucopyranosyl-carbamoyl)butyrate；methyl 5-oxo-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino]pentanoate
• 化学式: C₁₂H₂₁NO₈
• 分子量: 307.301
• InChiKey: KREJVFLGESYPGC-UJDFUTJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(trimethyl-lambda5-phosphanylidene)amino]oxan-2-yl]methyl acetate 在 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 生成 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

文献信息

• Stereoselective synthesis of glycosyl amides by traceless Staudinger ligation of unprotected glycosyl azides
  作者：Filippo Nisic、Anna Bernardi

  DOI：10.1016/j.carres.2008.04.023

  日期：2008.7

  The stereoconservative Staudinger ligation of unprotected alpha- and beta-glucosyl azides with diphenylphosphanyl-phenyl esters to afford alpha- and beta-glucosyl amides is described.

  描述了未保护的α-和β-葡糖基叠氮化物与二苯基膦基-苯基酯的立体保守Staudinger连接，得到α-和β-葡糖基酰胺。
• Synthesis of N-(β-d-glucopyranosyl) monoamides of dicarboxylic acids as potential inhibitors of glycogen phosphorylase
  作者：Katalin Czifrák、Zsuzsa Hadady、Tibor Docsa、Pál Gergely、Jürgen Schmidt、Ludger Wessjohann、László Somsák

  DOI：10.1016/j.carres.2006.03.002

  日期：2006.6

  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.