1-(2,3-dideoxy-α-D-glycero-pent-2-enopyranosyloxy)-12-(2,3-dideoxy-β-D-glycero-pent-2-enopyranosyloxy)dodecane | 1078737-07-1

• 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-(2,3-dideoxy-α-D-glycero-pent-2-enopyranosyloxy)-12-(2,3-dideoxy-β-D-glycero-pent-2-enopyranosyloxy)dodecane
• 英文别名: (3S,6R)-6-[12-[[(3S,6S)-3-hydroxy-3,6-dihydro-2H-pyran-6-yl]oxy]dodecoxy]-3,6-dihydro-2H-pyran-3-ol
• CAS: 1078737-07-1
• 化学式: C₂₂H₃₈O₆
• 分子量: 398.54
• InChiKey: GPCBDYYOLYAUMF-MYGLTJDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-(4-O-acetyl-2,3-dideoxy-α-D-glycero-pent-2-enopyranosyloxy)-12-(4-O-acetyl-2,3-dideoxy-β-D-glycero-pent-2-enopyranosyloxy)dodecane 在 甲醇 、 sodium methylate 作用下， 以37%的产率得到1-(2,3-dideoxy-α-D-glycero-pent-2-enopyranosyloxy)-12-(2,3-dideoxy-β-D-glycero-pent-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 and Self-Assembly of Glycal-Based Bolaforms
  作者：Joseph J. Bozell、Nathan C. Tice、Nibedita Sanyal、David Thompson、Jong-Mok Kim、Sébastien Vidal

  DOI：10.1021/jo801341g

  日期：2008.11.21

  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.