1,12-bis(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyloxy)dodecane | 212377-41-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 1,12-bis(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyloxy)dodecane
• 英文别名: [(2R,3S,6S)-3-acetyloxy-6-[12-[[(2R,3S,6S)-3-acetyloxy-2-(acetyloxymethyl)-3,6-dihydro-2H-pyran-6-yl]oxy]dodecoxy]-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 212377-41-8
• 化学式: C₃₂H₅₀O₁₂
• 分子量: 626.742
• InChiKey: UIIVIHAVGHLUHU-XPCOYVNDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  44
• 可旋转键数：
  25
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1,12-bis(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyloxy)dodecane 在 甲醇 、 sodium methylate 作用下， 以74%的产率得到1,12-bis(2,3-dideoxy-α-D-erythro-hex-2-enopyranosyloxy)dodecane
  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：

  1,12-十二烷二醇 、 乙酰化葡萄烯糖 在 碘 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到1,12-bis(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyloxy)dodecane
  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

文献信息

• Synthesis of Glycoside Derivatives Employing the Ferrier Rearrangement
  作者：Eusebius Wieczorek、Joachim Thiem

  DOI：10.1080/07328309808002352

  日期：1998.5.1

  Various glycals underwent smooth Lewis acid-catalysed allylic rearrangement reactions with O-nucleophiles to yield 2,3-unsaturated glycoside derivatives. In the hexose series predominantly alpha-D-, and in the pentose series beta-D-anomers resulted. Among others omega-cyano- as well as omega-benzyloxycarbonylamino functionalised alcohols could be used successfully. With diols the corresponding 1,1'-bridged disaccharides could be obtained.