dodecyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside | 1078736-96-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: dodecyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
• 英文别名: 6-dodecyloxy-2-hydroxymethyl-3,6-dihydro-2H-pyran-3-ol；(2R,3S,6S)-6-dodecoxy-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol
• CAS: 1078736-96-5
• 化学式: C₁₈H₃₄O₄
• 分子量: 314.466
• InChiKey: HEIHMDCWTYXHEA-KSZLIROESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  22
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dodecyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以74%的产率得到dodecyl 2,3-anhydro-α-D-allo-hexopyranoside
  参考文献：
  名称：

  评估十二烷基糖苷对炭疽芽孢杆菌的抗菌活性的最佳脱氧模式

  摘要：

  对抗抗生素耐药性的出现有赖于替代抗生素的开发。设计了新的十二烷基脱氧和双脱氧糖苷的方法，并通过芽孢杆菌（Bacillus spp）对化合物进行了测试。和粪肠球菌。4,6-去氧合模式对所有受试微生物的糖苷活性最高。

  DOI：

  10.1002/ejoc.201801764
• 作为产物：
  描述：

  dodecyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 在 甲醇 、 sodium methylate 作用下， 生成 dodecyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
  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.
• Assessing the Optimal Deoxygenation Pattern of Dodecyl Glycosides for Antimicrobial Activity Against<i>Bacillus anthracis</i>
  作者：Catarina Dias、Alice Martins、Ana Pelerito、Maria C. Oliveira、Marialessandra Contino、Nicola A. Colabufo、Amélia P. Rauter

  DOI：10.1002/ejoc.201801764

  日期：2019.3.31

  against antibiotic resistance emergence relies on the development of alternative antibiotics. Approaches towards new dodecyl deoxy and dideoxy glycosides were devised and compounds tested over Bacillus spp. and Enterococcus faecalis. The 4,6‐dideoxygenation pattern gave the most active glycoside against all tested microbes.

  对抗抗生素耐药性的出现有赖于替代抗生素的开发。设计了新的十二烷基脱氧和双脱氧糖苷的方法，并通过芽孢杆菌（Bacillus spp）对化合物进行了测试。和粪肠球菌。4,6-去氧合模式对所有受试微生物的糖苷活性最高。