N-[10-(α-D-mannopyranosyloxy)decyl]-N'-[ω-azidohexa(ethylene glycol)]thiourea | 1227080-56-9

• 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-[10-(α-D-mannopyranosyloxy)decyl]-N'-[ω-azidohexa(ethylene glycol)]thiourea
• 英文别名: 1-[2-[2-[2-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl]-3-[10-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxydecyl]thiourea
• CAS: 1227080-56-9
• 化学式: C₃₁H₆₁N₅O₁₂S
• 分子量: 727.918
• InChiKey: AWBRTAPUWAPACH-ZNOUKXQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  49
• 可旋转键数：
  34
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  225
• 氢给体数：
  6
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  [(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-[10-[2-[2-[2-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethylcarbamothioylamino]decoxy]oxan-2-yl]methyl acetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以78%的产率得到N-[10-(α-D-mannopyranosyloxy)decyl]-N'-[ω-azidohexa(ethylene glycol)]thiourea
  参考文献：
  名称：

  Glyco-SAMs by ‘Dual Click’: Thiourea-Bridged Glyco-OEG Azides for Cycloaddition on Surfaces

  摘要：

  A series of NCS-functionalized sugars were synthesized and used in a thiourea-bridging reaction with aminohexa(ethylene glycol) azide [H2N(EG)(6)N-3], a bifunctional oligo(ethylene glycol) derivative, which can be used as key intermediate for the fabrication of biorepulsive glyco-SAMs by a 'dual click' approach. Glyco-SAMs can serve as defined glycocalyx models for the study of carbohydrate-protein interactions. The copper(I)-catalyzed 1,3-dipolar cycloaddition reaction of the obtained glyco-OEG azides was exemplified, which can be used to modify preformed monolayers 'on SAM'.

  DOI：

  10.1055/s-0029-1218611

文献信息

• Glyco-SAMs by ‘Dual Click’: Thiourea-Bridged Glyco-OEG Azides for Cycloaddition on Surfaces
  作者：Thisbe Lindhorst、Carsten Grabosch、Mike Kleinert

  DOI：10.1055/s-0029-1218611

  日期：2010.3

  A series of NCS-functionalized sugars were synthesized and used in a thiourea-bridging reaction with aminohexa(ethylene glycol) azide [H2N(EG)(6)N-3], a bifunctional oligo(ethylene glycol) derivative, which can be used as key intermediate for the fabrication of biorepulsive glyco-SAMs by a 'dual click' approach. Glyco-SAMs can serve as defined glycocalyx models for the study of carbohydrate-protein interactions. The copper(I)-catalyzed 1,3-dipolar cycloaddition reaction of the obtained glyco-OEG azides was exemplified, which can be used to modify preformed monolayers 'on SAM'.