N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl) benzamide | 13199-09-2

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl) benzamide
• 英文别名: N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)benzamide；[(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-benzamidooxan-2-yl]methyl acetate
• CAS: 13199-09-2
• 化学式: C₂₁H₂₆N₂O₉
• 分子量: 450.445
• InChiKey: OLTJWGSUUJOHTP-DRJBRKBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  146
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  苯甲酰氯 、 2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-Β-D-吡喃葡萄糖酰基叠氮化物 在 三甲基膦 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 336.0h， 以43%的产率得到N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl) benzamide
  参考文献：
  名称：

  Synthesis of N-(β-D-glucopyranosyl)- and N-(2-acetamido-2-deoxy-β-D-glucopyranosyl) amides as inhibitors of glycogen phosphorylase

  摘要：

  2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl- and 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl azides were transformed into the corresponding per-O-acetylated N-(beta-D-glycopyranosyl) amides via a PMe3 mediated Staudinger protocol (generation of N-(beta-D-glycopyranosyl)imino-trimethylphosphoranes followed by acylation with carboxylic acids, acid chlorides or anhydrides). The deprotected compounds obtained by Zemplen deacetylation were evaluated as inhibitors of rabbit muscle glycogen phosphorylase b. The best inhibitor of this series has been N-(beta-D-glucopyranosyl) 3-(2-naphthyl)-propenoic amide (K-i = 3.5 muM). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.013

文献信息

• Facile synthesis of N-glycosyl amides using a N-glycosyl-2,4-dinitrobenzenesulfonamide and thioacids
  作者：Rommel S. Talan、Aditya K. Sanki、Steven J. Sucheck

  DOI：10.1016/j.carres.2009.07.002

  日期：2009.10

  N-Glucosyl-2,4-dinitrobenzenesulfonamide was prepared from N-acetyl-D-glucosamine and 2,4-dinitrobenzenesulfonyl chloride. Amidation of several thioacids using the N-glucosylsulfonamide donor proceeded smoothly to give the desired N-glucosylamides in good to high yields. The amidation reactions were carried out at room temperature, under mild conditions, and were completed in a very short time. Published by Elsevier Ltd.