{2-[2-((2R,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-ethoxy]-ethoxy}-acetic acid | 597533-75-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: {2-[2-((2R,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-ethoxy]-ethoxy}-acetic acid
• 英文别名: 2-[2-[2-[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]sulfanylethoxy]ethoxy]acetic acid
• CAS: 597533-75-0
• 化学式: C₂₀H₃₀O₁₃S
• 分子量: 510.516
• InChiKey: HMIFERHOYLAAIN-LFZDHENXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  34
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  196
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  {2-[2-((2R,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-ethoxy]-ethoxy}-acetic acid 在 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 (S)-2,6-Bis-(2-{2-[2-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-ethoxy]-ethoxy}-acetylamino)-hexanoic acid
  参考文献：
  名称：

  Synthesis of an amphiphilic tetraantennary mannosyl conjugate and incorporation into liposome carriers

  摘要：

  We have synthesized a novel conjugate (Man(4)K(3)DOG) composed of a tetramannosyl head group connected, via a polyethylene glycol spacer, to a lipid moiety. This amphiphilic molecule was easily incorporated into the bilayers of liposomes. As expected from the clustering effect, such multivalent mannose residues when exposed on the surface of the vesicles showed much higher binding affinity for Concanavalin A than their monomannosyl analogue. Mannosylated liposomes prepared with the tetravalent antenna could be promising carriers for e.g., loading dendritic cells with antigens for vaccination purposes. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00472-4
• 作为产物：
  描述：

  {2-(2-mercapto-ethoxy)ethoxy}acetic acid 、 1,2,3,4,6-O-五乙酰基-Alpha-甘露糖 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以40%的产率得到{2-[2-((2R,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-ethoxy]-ethoxy}-acetic acid
  参考文献：
  名称：

  Synthesis of an amphiphilic tetraantennary mannosyl conjugate and incorporation into liposome carriers

  摘要：

  We have synthesized a novel conjugate (Man(4)K(3)DOG) composed of a tetramannosyl head group connected, via a polyethylene glycol spacer, to a lipid moiety. This amphiphilic molecule was easily incorporated into the bilayers of liposomes. As expected from the clustering effect, such multivalent mannose residues when exposed on the surface of the vesicles showed much higher binding affinity for Concanavalin A than their monomannosyl analogue. Mannosylated liposomes prepared with the tetravalent antenna could be promising carriers for e.g., loading dendritic cells with antigens for vaccination purposes. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00472-4