dodecyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside | 260549-45-9

• 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 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
• 英文别名: [(2R,3S,6S)-3-acetyloxy-6-dodecoxy-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 260549-45-9
• 化学式: C₂₂H₃₈O₆
• 分子量: 398.54
• InChiKey: NBZYMLQPYALJBS-BDTNDASRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  28
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  十二烷醇 、 乙酰化葡萄烯糖 在 碘 作用下， 以 二氯甲烷 为溶剂， 生成 dodecyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 、 Acetic acid (2R,3S,6R)-2-acetoxymethyl-6-dodecyloxy-3,6-dihydro-2H-pyran-3-yl ester
  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

• Alkyl deoxy-arabino-hexopyranosides: Synthesis, surface properties, and biological activities
  作者：Filipa V.M. Silva、Margarida Goulart、Jorge Justino、Ana Neves、Fernando Santos、João Caio、Susana Lucas、Ana Newton、Diana Sacoto、Ester Barbosa

  DOI：10.1016/j.bmc.2008.01.020

  日期：2008.4.1

  Octyl and dodecyl glycosides possessing 2-deoxy-arabino-hexopyranoside moieties belonging to the D-and L-series in their alpha- and beta-forms were synthesized by reaction of an acetyl protected glycal with octanol or dodecanol, catalyzed by triphenylphosphine hydrobromide, followed by deprotection. Their surface properties were studied and discussed in terms of the adsorption and aggregation parameters, pC(20), CMC, and gamma(CMC). The antimicrobial activities were assessed using the paper disk diffusion and broth dilution methods. Both the octyl and dodecyl 2-deoxy beta-D-glycosides inhibited significantly Enterococcus faecalis, a microbe also highly susceptible to dodecyl 2,6-dideoxy-alpha-L-arabino-hexopyranoside. This compound was particularly active against Bacillus cereus and Bacillus subtilis, presenting for both Bacillus species a minimal inhibitory concentration of the same order of magnitude and a minimal lethal concentration even smaller than that obtained for chloramphenicol, a bioactivity which remained unaltered after 1 year solution storage at 4 degrees C. In addition, activity over Listeria monocytogenes was also observed. Direct cytotoxicity and genotoxicity of the glycosides were determined by proliferative index (mitotic index) evaluation in peripheral human lymphocytes of healthy donors. All compounds induced acute toxicity effects, and the response was dose dependent for the alpha-anomer of both the alkyl 2-deoxy-arabino-hexopyranosides and for the corresponding dodecyl beta-anomer, what suggests that non-toxic but still bioactive concentrations may be found for these compounds. (C) 2008 Elsevier Ltd. All rights reserved.
• Konstantinovic; Predojevic; Gojkovic, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 12, p. 1242 - 1244
  作者：Konstantinovic、Predojevic、Gojkovic、Ratkovic、Mojsilovic、Pavlovic

  DOI：——

  日期：——