N'-phenyl-N-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl urea | 904672-02-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N'-phenyl-N-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl urea
• 英文别名: 1-phenyl-3-[(2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]urea
• CAS: 904672-02-2
• 化学式: C₄₁H₄₂N₂O₆
• 分子量: 658.794
• InChiKey: FLHKJWLSSAFINQ-DTQLOPILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  49
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  87.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  异氰酸苯酯 、 1-azido-1-deoxy-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose 在 三甲基膦 、 甲酸 、 水 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 以74%的产率得到N'-phenyl-N-2,3,4,6-tetra-O-benzyl-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

文献信息

• Direct Coupling of Amides and Urea to Glycosyl Halides Using Silver Triflate
  作者：Luz M. Rosado、Terence J. Meyerhoefer、Saqib M. Bett、Saba. Ilyas、Lubabalo. Bululu、Carla A. Martin、Troy W. Joseph、Michael De Castro

  DOI：10.1002/ejoc.201600350

  日期：2016.6

  We herein report the coupling of various amides and ureas to glycosyl halides in the presence of silver triflate at room temperature. A 1:1 mixture of α/β diastereomers was obtained when alkyl/heteroaryl amides and substituted ureas were added to gluco and galacto haloglycosides. The effect of temperature, halogen, protecting group of the sugar and substituent of the amide in the overall yields and

  我们在此报告了在室温下在三氟甲磺酸银存在下各种酰胺和脲与糖基卤化物的偶联。当将烷基/杂芳基酰胺和取代的脲加入葡糖和半乳糖卤代糖苷时，得到 1:1 的 α/β 非对映体混合物。还探讨了温度、卤素、糖的保护基团和酰胺的取代基对反应的总产率和立体选择性的影响。当在反应中使用乙酰保护的葡萄糖醛酸酰胺时，在室温下以良好的收率获得了相应假双糖的β端基异构体作为主要异构体。使用 HeLa 癌细胞对新合成的化合物进行了活力研究。本研究还讨论了获得的结果。