[(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 | 1227080-40-1

• 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: [(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
• CAS: 1227080-40-1
• 化学式: C₃₉H₆₉N₅O₁₆S
• 分子量: 896.067
• InChiKey: DVTNZLYBUCOWKY-DSVGPAFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  61
• 可旋转键数：
  42
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  250
• 氢给体数：
  2
• 氢受体数：
  19

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  O-(2-氨基乙基)-O'-(2-叠氮乙基)戊乙二醇 、 10-isothiocyanatodecyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以50%的产率得到[(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
  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