N'-phenyl-N-α-D-glucopyranosyl urea | 904672-05-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N'-phenyl-N-α-D-glucopyranosyl urea
• CAS: 904672-05-5
• 化学式: C₁₃H₁₈N₂O₆
• 分子量: 298.296
• InChiKey: LKCDLOUQOJQBRX-ZIQFBCGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.39
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  131.28
• 氢给体数：
  6.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N'-phenyl-N-α-D-glucopyranosyl urea 、 乙酸酐 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 反应 18.0h， 以80%的产率得到N'-phenyl-N-2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl urea
  参考文献：
  名称：

  A facile stereoselective synthesis of α-glycosyl ureas

  摘要：

  alpha-Glycosyl ureas can be synthesised directly from tetra-O-benzyl glycosyl azides and isocyanates, using a one-pot procedure that is simple and general in scope. The benzyl protecting groups are easily removed from the urea products by catalytic hydrogenation. The synthesised alpha-glycosyl ureas represent a new class of neo-glycoconjugates with the potential of being resistant towards carbohydrate processing enzymes. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.042
• 作为产物：
  描述：

  N'-phenyl-N-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl urea 在 palladium on activated charcoal 氢气 作用下， 以 N,N-二甲基乙酰胺 、 水 、 溶剂黄146 为溶剂， 以85%的产率得到N'-phenyl-N-α-D-glucopyranosyl urea
  参考文献：
  名称：

  A facile stereoselective synthesis of α-glycosyl ureas

  摘要：

  alpha-Glycosyl ureas can be synthesised directly from tetra-O-benzyl glycosyl azides and isocyanates, using a one-pot procedure that is simple and general in scope. The benzyl protecting groups are easily removed from the urea products by catalytic hydrogenation. The synthesised alpha-glycosyl ureas represent a new class of neo-glycoconjugates with the potential of being resistant towards carbohydrate processing enzymes. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.042