octyl 2-deoxy-α-D-arabino-hexopyranoside | 144467-15-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: octyl 2-deoxy-α-D-arabino-hexopyranoside
• 英文别名: n-octyl α-2-deoxy-D-glucopyranoside；octyl 2-deoxy-α-D-glucopyranoside；octyl 2-deoxy-α-D-glycoside；C8-2d-α-Glc；(2R,3S,4R,6S)-2-(hydroxymethyl)-6-octoxyoxane-3,4-diol
• CAS: 144467-15-2
• 化学式: C₁₄H₂₈O₅
• 分子量: 276.373
• InChiKey: YZTAWEJTVSMTRO-MQYQWHSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  9
• 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：

  octyl 2-deoxy-α-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 octyl 2,6-dideoxy-α-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：

  辛醇 在 sodium methylate 、 三苯基膦氢溴酸盐 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.75h， 生成 octyl 2-deoxy-α-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

• Ionic liquid promoted atom economic glycosylation under Lewis acid catalysis
  作者：Jacques Augé、Gwenaëlle Sizun

  DOI：10.1039/b904692e

  日期：——

  Straightforward glycosylation of various alcohols with unprotected and non-activated monosaccharides were performed under scandium triflate catalysis. Rate and yield of glycosylation were highly improved when using 1-butyl-3-methylimidazolium trifluoromethanesulfonate as a green solvent. This ionic liquid was allowed to be recycled at least three times without loss of activity. The possibility of drastically reducing the amounts of catalyst (down to 1 mol%) and aglycone (down to 1 equiv) when performing the reaction in ionic liquid opens new perspectives in O-glycosylation, as a direct coupling between an aglycone and free sugars.

  在钪三氟甲磺酸盐催化下，对各种醇与未保护和非活化的单糖进行了直接的糖苷化反应。当使用1-丁基-3-甲基咪唑三氟甲磺酸盐作为绿色溶剂时，糖苷化的反应速率和产率得到了显著提高。该离子液体可至少回收使用三次而不会失去活性。在离子液体中进行反应时，可以显著减少催化剂的用量（低至1 mol%）和糖苷的用量（低至1当量），这为O-糖苷化的直接耦合提供了新的前景，能够在糖苷和游离糖之间实现直接连接。
• Iodoacetoxylation Reaction: A Convenient Route to α-Glycosides in the 2-Iodo and 2-Deoxy Series
  作者：Dominique Lafont、Paul Boullanger、Michael Rosenzweig

  DOI：10.1080/07328309808002360

  日期：1998.12

  Iodoacetoxylation of 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol (tri-O-acetyl-D-glucal)(1) and 3,4-di-O-acetyl-1,5-anhydro-2,6-dideoxy-L-arabino-hex-1-enitol (di-O-acetyl-L-rhamnal) (3) gave the alpha-1,2-trans-1-O-acetyl-2-deoxy-2-iodo adducts with high stereoselectivities and good yields, in accordance with the results reported on 3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-1,5-anhydro-2-deoxy-D-arahino-hex-1-enitol (hexa-O-acetyl lactal) (2). The alpha-1,2-trans adducts were reacted with an excess of alcohol in the presence of trimethylsilyl trifluoromethanesulfonate affording the corresponding alpha-1,2-trans-2-deoxy-2-iodo-glycopyranoside in good yields. The octyl 2-deoxy-2-iodo-alpha-D-glycosides 10 and 11 prepared in two steps from the glycals 1 and 2 were deiodinated and deacetylated, giving 28 and 29, and the physicochemical-properties (cmc) of 29 are reported.
• 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.
• Enzymatic synthesis of alkyl α-2-deoxyglucosides by alkyl alcohol resistant α-glucosidase from Aspergillus niger
  作者：Young-Min Kim、Masayuki Okuyama、Haruhide Mori、Hiroyuki Nakai、Wataru Saburi、Seiya Chiba、Atsuo Kimura

  DOI：10.1016/j.tetasy.2004.11.046

  日期：2005.1

  Aspergillus niger alpha-glucosidase (ANGase) was used for an efficient syntheses of alkyl alpha-D-2-deoxyglucosides (A2DGs) and for regioselectivity studies of alkoxy-hydro additions Of D-glucal in the presence of alkyl alcohols. ANGase showed a high stability with respect to the high concentration of alkyl alcohols. The reaction conditions were optimized for pH, temperature, alkyl alcohol concentration, and D-glucal concentration. On the basis of MS and NMR analyses, A2DGs were confirmed to have only an alpha-2deoxyglucosidic bond and the two-dimensional NMR (HMBC) spectra showed to be made up of 2-deoxyglucosyl and alkyl moieties. (C) 2004 Elsevier Ltd. All rights reserved.