N'-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-3-aminopropionamide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N'-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-3-aminopropionamide
• 英文别名: N-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-3-aminopropanamide
• 化学式: C₁₁H₂₁N₃O₆
• 分子量: 291.304
• InChiKey: VIVIBDGRWFXJDG-NENRSDFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  154
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  D-GlcNAc 在 碳酸氢铵 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 56.0h， 生成 N'-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-3-aminopropionamide
  参考文献：
  名称：

  Synthesis of N4-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-l-asparagine analogues. n-Butyramide, 3-chloropropionamide, 3-aminopropionamide, and isovaleramide analogues

  摘要：

  The syntheses of four analogues of N-4-(2-acetamido-2-deoxy-beta -D-glucopyranosyl)-L-asparagine are described. Activated carboxylic acids were reacted with 2-acetamido-2-deoxy-beta -D-glucopyranosylamine, n-Butyric anhydride gave N-(2-acetamido-2-deoxy-beta -D-glucopyranosyl)-n-butyramide. 3-Chloropropionic anhydride was synthesized from 3-chloropropionic acid and gave N-(2-acetamido-2-deoxy-beta -D-glucopyranosyl)-3-chloropropionamide. Equilibration of the latter with ammonium bicarbonate gave N-1-(2-acetamido-2-deoxy-beta -D-glucopyranosyl)-3-aminopropionamide. Succinimidyl isovalerate was synthesized and gave N-(2-acetamido-2-deoxy-beta -D-glucopyranosyl)isovaleramide. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00057-x

文献信息

• Synthesis of N4-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-l-asparagine analogues. n-Butyramide, 3-chloropropionamide, 3-aminopropionamide, and isovaleramide analogues
  作者：Jerry J. Kaylor、John M. Risley

  DOI：10.1016/s0008-6215(01)00057-x

  日期：2001.4

  The syntheses of four analogues of N-4-(2-acetamido-2-deoxy-beta -D-glucopyranosyl)-L-asparagine are described. Activated carboxylic acids were reacted with 2-acetamido-2-deoxy-beta -D-glucopyranosylamine, n-Butyric anhydride gave N-(2-acetamido-2-deoxy-beta -D-glucopyranosyl)-n-butyramide. 3-Chloropropionic anhydride was synthesized from 3-chloropropionic acid and gave N-(2-acetamido-2-deoxy-beta -D-glucopyranosyl)-3-chloropropionamide. Equilibration of the latter with ammonium bicarbonate gave N-1-(2-acetamido-2-deoxy-beta -D-glucopyranosyl)-3-aminopropionamide. Succinimidyl isovalerate was synthesized and gave N-(2-acetamido-2-deoxy-beta -D-glucopyranosyl)isovaleramide. (C) 2001 Elsevier Science Ltd. All rights reserved.