[(2R,3S,6S)-3-acetyloxy-6-(12-hydroxydodecoxy)oxan-2-yl]methyl acetate | 1078736-94-3

• 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,3S,6S)-3-acetyloxy-6-(12-hydroxydodecoxy)oxan-2-yl]methyl acetate
• CAS: 1078736-94-3
• 化学式: C₂₂H₄₀O₇
• 分子量: 416.555
• InChiKey: HOFGKECNFGUDOP-BDTNDASRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(2R,3S,6S)-3-acetyloxy-6-(12-hydroxydodecoxy)oxan-2-yl]methyl acetate 、 乙酰化葡萄烯糖 在 碘 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到
  参考文献：
  名称：

  Synthesis and Self-Assembly of Glycal-Based Bolaforms

  摘要：

  Glycal-based bolaforms serve as synthetically flexible components of molecular self-assembly. The compounds are prepared in good yield by a Ferrier reaction between triacetylglucal or -galactal or diacetylxylal and a long chain alpha,omega-diol, followed by deacetylation under Zemplen conditions. The reactions are stereoselective and preferentially afford the alpha-diastereomer. The bolaforms undergo self-assembly in water or water/dioxane solution to give a variety of nanostructures. In solution, bolaforms with C-8 or C-10 chains between glucal headgroups form nanoscale vesicles. In contrast, bolaforms with C-12 chains exhibit lower solubility and a dynamic self-assembly, forming several different nanoscale structures. However, the solid-state structures of C-12 bolaform isomers adopt shapes very similar to those of bolaforms possessing more extensive hydrogen-bonding networks, indicating that multiple hydrogen bonds in solution are important to formation of stable, discrete nanostructures but that only a few key intermolecular interactions between bolaform headgroups are necessary to determine the structure in the solid state. The diversity and differentiation of the functional groups present in glycal-based bolaforms suggest that they could be useful probes of the various noncovalent forces controlling the structure of new nanomaterials.

  DOI：

  10.1021/jo801341g
• 作为产物：
  描述：

  在 5% Pd/C 、 氢气 作用下， 生成 [(2R,3S,6S)-3-acetyloxy-6-(12-hydroxydodecoxy)oxan-2-yl]methyl acetate
  参考文献：
  名称：

  Synthesis and Self-Assembly of Glycal-Based Bolaforms

  摘要：

  Glycal-based bolaforms serve as synthetically flexible components of molecular self-assembly. The compounds are prepared in good yield by a Ferrier reaction between triacetylglucal or -galactal or diacetylxylal and a long chain alpha,omega-diol, followed by deacetylation under Zemplen conditions. The reactions are stereoselective and preferentially afford the alpha-diastereomer. The bolaforms undergo self-assembly in water or water/dioxane solution to give a variety of nanostructures. In solution, bolaforms with C-8 or C-10 chains between glucal headgroups form nanoscale vesicles. In contrast, bolaforms with C-12 chains exhibit lower solubility and a dynamic self-assembly, forming several different nanoscale structures. However, the solid-state structures of C-12 bolaform isomers adopt shapes very similar to those of bolaforms possessing more extensive hydrogen-bonding networks, indicating that multiple hydrogen bonds in solution are important to formation of stable, discrete nanostructures but that only a few key intermolecular interactions between bolaform headgroups are necessary to determine the structure in the solid state. The diversity and differentiation of the functional groups present in glycal-based bolaforms suggest that they could be useful probes of the various noncovalent forces controlling the structure of new nanomaterials.

  DOI：

  10.1021/jo801341g