10-bromodecyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside | 1227080-21-8

• 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: 10-bromodecyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-(10-bromodecoxy)oxan-2-yl]methyl acetate
• CAS: 1227080-21-8
• 化学式: C₂₄H₃₉BrO₁₀
• 分子量: 567.472
• InChiKey: AUPHQPBWJVOEMO-DJCPXJLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  35
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  10-bromodecyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 sodium azide 、 四丁基溴化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 以85%的产率得到10-azidodecyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
  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：

  10-溴-1-癸醇 、 2,3,4,6-四-O-乙酰基-α-D-吡喃甘露糖 三氯乙酰亚胺酯 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到10-bromodecyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
  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