dodecyl 2-deoxy-β-D-arabino-hexopyranoside | 1033005-30-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dodecyl 2-deoxy-β-D-arabino-hexopyranoside
• 英文别名: C12-2d-β-Glc；(2R,3S,4R,6R)-6-dodecoxy-2-(hydroxymethyl)oxane-3,4-diol
• CAS: 1033005-30-9
• 化学式: C₁₈H₃₆O₅
• 分子量: 332.481
• InChiKey: YEUOFJKXMLMMRZ-TVFCKZIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dodecyl 2-deoxy-β-D-arabino-hexopyranoside 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 74.0h， 生成 dodecyl 2,6-dideoxy-β-D-arabinohexopyranoside
  参考文献：
  名称：

  将表面活性脱氧糖苷的生物活性调整为结构：抗菌活性与通过分子对接合理化的选择性胆碱酯酶抑制

  摘要：

  新的辛基/十二烷基 2,6-二脱氧-D-阿拉伯-己基吡喃糖苷通过一种简单但有效的方法合成，该方法基于三苯基膦氢溴酸盐催化的糖醇与醇的反应、脱保护、区域选择性甲苯磺酰化和还原。根据吸附和聚集参数评估它们的表面活性特性，并与 2-脱氧-D-糖苷和 2,6-双脱氧-L-糖苷进行比较。6 位脱氧导致临界胶束浓度降低，吸附效率 (pC20) 增加，促进聚集比吸附更有效。关于抗菌活性，十二烷基 2,6-二脱氧-α-L-阿拉伯-吡喃己糖苷是对炭疽芽孢杆菌最具活性的化合物（MIC 25 μM），而其对映体的 MIC 值为 50 μM。两者 2, 6-双脱氧糖苷对蜡样芽孢杆菌、枯草芽孢杆菌、粪肠球菌和单核细胞增生李斯特菌有活性。相比之下，没有一种 2-脱氧糖苷具有显着活性。这些结果和表面活性数据表明聚集是抗菌活性的关键问题。除了感染，阿尔茨海默病还威胁着老年人口。在寻找丁酰胆碱酯酶 (BChE) 选择性抑制作用的过程中，使用

  DOI：

  10.1002/ejoc.201201520
• 作为产物：
  描述：

  dodecyl 3,4,6-tri-O-acetyl-2-deoxy-β-D-arabino-hexopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.75h， 以97%的产率得到dodecyl 2-deoxy-β-D-arabino-hexopyranoside
  参考文献：
  名称：

  将表面活性脱氧糖苷的生物活性调整为结构：抗菌活性与通过分子对接合理化的选择性胆碱酯酶抑制

  摘要：

  新的辛基/十二烷基 2,6-二脱氧-D-阿拉伯-己基吡喃糖苷通过一种简单但有效的方法合成，该方法基于三苯基膦氢溴酸盐催化的糖醇与醇的反应、脱保护、区域选择性甲苯磺酰化和还原。根据吸附和聚集参数评估它们的表面活性特性，并与 2-脱氧-D-糖苷和 2,6-双脱氧-L-糖苷进行比较。6 位脱氧导致临界胶束浓度降低，吸附效率 (pC20) 增加，促进聚集比吸附更有效。关于抗菌活性，十二烷基 2,6-二脱氧-α-L-阿拉伯-吡喃己糖苷是对炭疽芽孢杆菌最具活性的化合物（MIC 25 μM），而其对映体的 MIC 值为 50 μM。两者 2, 6-双脱氧糖苷对蜡样芽孢杆菌、枯草芽孢杆菌、粪肠球菌和单核细胞增生李斯特菌有活性。相比之下，没有一种 2-脱氧糖苷具有显着活性。这些结果和表面活性数据表明聚集是抗菌活性的关键问题。除了感染，阿尔茨海默病还威胁着老年人口。在寻找丁酰胆碱酯酶 (BChE) 选择性抑制作用的过程中，使用

  DOI：

  10.1002/ejoc.201201520

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.
• Effect of the C-2 hydroxyl group on the mesomorphism of alkyl glycosides: synthesis and thermotropic behavior of alkyl 2-deoxy-d-arabino-hexopyranosides
  作者：Madan Kumar Singh、Narayanaswamy Jayaraman、D.S. Shankar Rao、S. Krishna Prasad

  DOI：10.1016/j.chemphyslip.2008.07.008

  日期：2008.10

  A homologous series of alkyl 2-deoxy-alpha-D-arabino-hexopyranosides and alkyl 2-deoxy-beta-D-arabino-hexopyranosides were synthesized, upon glycosylation of 1-alkanols (from C-8 to C-18 alkanols) with ethyl 2-deoxy-3,4,6-tri-O-acetyl-1-thio-D-arabino-hexopyranoside, followed by a deprotection. The thermotropic behavior of these new types of alkyl glycosides was investigated. It was observed that the beta-anomers of these alkyl glycosides, bearing nonyl to tetradecyl alkyl chain are mesomorphic, exhibiting monotropic smectic A phase. In contrast, the alpha-anomers are all non-mesomorphic. An effort to identify the liquid crystalline behavior of binary mixtures of the alpha- and beta-anomers was undertaken and it was found that mixtures containing equimolar amounts of the anomers exhibited rnesomorphic behavior. A fine balance of the hydrophilic and hydrophobic components within the molecule is also found to be important for the alkyl 2-deoxy glycosides to form the mesophase. (C) 2008 Elsevier Ireland Ltd. All rights reserved.