十烷基-β-D-硫代吡喃葡萄糖苷 | 98854-16-1

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 十烷基-β-D-硫代吡喃葡萄糖苷
• 中文别名: 癸基-Β-D-硫代吡喃葡萄糖苷；十烷基-Β-D-硫代吡喃葡萄糖苷
• 英文名称: n-decyl-β-D-thioglucopyranoside
• 英文别名: n-Decyl 1-thio-β-D-glucopyranoside；β-thiodecyl D-glucoside；decyl 1-thio-β-D-glucopyranoside；(2S,3R,4S,5S,6R)-2-(Decylthio)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol；(2S,3R,4S,5S,6R)-2-decylsulfanyl-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 98854-16-1
• 化学式: C₁₆H₃₂O₅S
• 分子量: 336.493
• InChiKey: WXUWOACRYZHYQL-LJIZCISZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  4-癸氧基苯甲醛 、 十烷基-β-D-硫代吡喃葡萄糖苷 在 甲烷磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Non-Amphiphilic Carbohydrate Liquid Crystals Containing an Intact Monosaccharide Moiety

  摘要：

  A chiral rigid moiety which forms the basis of a new class of non-amphiphilic carbohydrate liquid crystals has been developed. This moiety contains a fully intact glucopyranose ring embedded in a trans-decalin structure. The original carbohydrate is substituted so that only two hydroxyl groups are left, resulting in derivatives with reduced hydrophilicity. The substituents R and X-R' on the 4,6-O-ylidene beta-D-glucopyranoside are in the equatorial position and can be varied extensively, using straightforward synthetic procedures. Investigations as to the requirements for R and X-R' for inducing liquid-crystalline behavior have shown that at least one of the substituents should contain a large, polarizable aromatic moiety. An aromatic Schiff base fulfils this requirement.

  DOI：

  10.1080/10587259508038691
• 作为产物：
  描述：

  α-D(+)-五乙酰葡萄糖 在 磷化氢 、 sodium hydroxide 、 氢溴酸 、 溴 、 potassium carbonate 、 sodium hydrogensulfite 作用下， 以 甲醇 、 水 、 乙酸酐 、 丙酮 为溶剂， 反应 1.5h， 生成 十烷基-β-D-硫代吡喃葡萄糖苷
  参考文献：
  名称：

  Saito, Setsuo; Tsuchiya, Tomofusa, Chemical and pharmaceutical bulletin, 1985, vol. 33, # 2, p. 503 - 508

  摘要：

  DOI：

文献信息

• Synthesis and surface properties of alkyl β‑ ‑thioglucopyranoside
  作者：Xiubing Wu、Langqiu Chen、Fang Fu、Yulin Fan、Zhiqiang Luo

  DOI：10.1016/j.molliq.2018.11.134

  日期：2019.2

  Alkyl thioglycosides are a class of nonionic sugar-based sulfur-containing surfactants and bioreagents. The surfactants 1,2‑trans alkyl β‑d‑thioglucopyranosides with different alkyl chain length (n = 6–12) were stereoselectively prepared by the Helferich method. Their properties including HLB number, logP value, water solubility, foam property, emulsifying property, surface property and thermotropic

  烷基硫糖苷是一类非离子的基于糖的含硫表面活性剂和生物试剂。用Helferich方法立体选择性地制备了具有不同烷基链长（n = 6-12）的表面活性剂1,2-反烷基β - d-硫代吡喃葡萄糖苷。主要研究了它们的性质，包括HLB值，log P值，水溶性，泡沫性质，乳化性质，表面性质和热致液晶性质。结果表明，随着烷基链长的增加，log B值增加，其HLB值和水溶性降低。烷基β - d-硫葡糖苷已经不溶于n≥10的水中。在临界胶束浓度（CMC）时，两种β - d-硫代吡喃葡萄糖苷（n = 8、9）都将相关水溶液的表面张力降低至近29 mN·m -1。，它们还具有优异的起泡能力和泡沫稳定性。壬基β - d-硫代吡喃葡萄糖苷对正辛烷/水系统和甲苯/水系统均具有良好的乳化性能。观察到烷基β - d-硫代吡喃葡萄糖苷（n = 6-12）具有热致液晶特性。
• Preparation of S-glycoside surfactants and cysteine thioglycosides using minimally competent Lewis acid catalysis
  作者：Lajos Z. Szabó、Dillon J. Hanrahan、Evan M. Jones、Erin Martin、Jeanne E. Pemberton、Robin Polt

  DOI：10.1016/j.carres.2015.12.008

  日期：2016.3

  Here we report a method for the preparation of anomerically pure beta-S-glycopyranosides (1,2-trans-glycosides) from the corresponding peracetate donors. S-glycosylation was performed in CHCl3 at reflux in the presence of a catalytic amount of InBr3. Deacylation of the intermediate peracetates were achieved under Zemplen conditions. Five pyranose examples, monosaccharides D-glucose and D-galactose

  在这里，我们报告了一种从相应的过乙酸盐供体制备异头纯β-S-吡喃糖苷（1,2-反式糖苷）的方法。在催化量的 InBr3 存在下，在 CHCl3 中回流进行 S-糖基化。在 Zemplen 条件下实现中间体过乙酸酯的脱酰化。五个吡喃糖的例子，单糖 D-葡萄糖和 D-半乳糖和二糖纤维二糖、麦芽糖和乳糖，被用作供体，五种硫醇，包括 α/ω 二硫醇和 Fmoc-L-半胱氨酸被用作受体。报告了先前未描述的化合物的熔点、高分辨率 MS、αD 和 NMR 数据((1)H 和 (13)C，包括 COSY、HSQC 和 HMBC)。
• Towards the preparation of synthetic outer membrane vesicle models with micromolar affinity to wheat germ agglutinin using a dialkyl thioglycoside
  作者：Dimitri Fayolle、Nathalie Berthet、Bastien Doumeche、Olivier Renaudet、Peter Strazewski、Michele Fiore

  DOI：10.3762/bjoc.15.90

  日期：——

  ability towards wheat germ agglutinin was measured by competitive enzyme-linked lectin assays. One of the synthetic compounds presenting two GlcNAc units showed the highest inhibitory effect of this study with an IC50 of 11 µM corresponding to a 3182-fold improvement compared to GlcNAc. These synthetic molecules were used to produce giant vesicles, alone or in mixture with phospholipids, mimicking bacterial

  通过硫醇-烯偶联以中等至良好的收率（40-85％）制备了一系列带有葡萄糖和N-乙酰氨基葡糖残基的烷基硫代糖苷和烷基硫代二糖苷。通过竞争性酶联凝集素测定法测定了它们对小麦胚芽凝集素的结合能力。具有两个GlcNAc单位的一种合成化合物显示出最高的抑制效果，IC 50为11 µM，与GlcNAc相比提高了3182倍。这些合成分子被用来单独或与磷脂混合产生巨大的囊泡，从而模仿具有潜在抗粘附特性的细菌外膜囊泡（OMV）。
• A Comparison of the Antibacterial Efficacy of Carbohydrate Lipid-like (Thio)Ether, Sulfone, and Ester Derivatives against Paenibacillus larvae
  作者：Veronika Šamšulová、Mária Šedivá、Juraj Kóňa、Jaroslav Klaudiny、Monika Poláková

  DOI：10.3390/molecules28062516

  日期：——

  than their decylated analogs. Thioglycosides were more efficient than glycosides and sulfones. The activity of the 6-O-ether derivatives was higher than that of their ester counterparts. Seven derivatives with dodecyl chain linked (thio)glycosidically or etherically at C-6 showed high efficacy against both P. larvae strains (MICs ranged from 12.5 μM to 50 μM). Their efficacies were similar or much higher

  类芽孢杆菌幼虫是美洲臭虫 (AFB) 的病原体，AFB 是影响蜜蜂幼虫和蛹发育的最严重的细菌性疾病。在这项研究中，评估了从具有 C10 或 C12 烷基链的 d-甘露糖、d-葡萄糖和 d-半乳糖衍生的 24 种（硫代）糖苷、糖基砜、6-O-酯和醚的文库的抗菌功效针对两种 P. 幼虫菌株。以最小抑制浓度 (MIC) 确定的受试化合物的功效差异很大。通常，发现十二烷基衍生物比它们的癸基化类似物更有效。硫苷比苷和砜更有效。6-O-醚衍生物的活性高于它们的酯对应物。在 C-6 处具有十二烷基链（硫代）糖苷或醚连接的七种衍生物显示出对两种 P. 幼虫菌株的高效（MIC 范围从 12.5 μM 到 50 μM）。它们的功效与已知对 P. larvae-lauric acid、monolaurin 和蜜蜂幼虫食物成分、10-hydroxy-2-decenoic acid 和 sebacic acid（MIC
• Aggregate with increased deformability, comprising at least three amphipats, for improved transport through semi-permeable barriers and for the non-invasive drug application in vivo, especially through the skin
  申请人：IDEA AG

  公开号：EP1815846A2

  公开（公告）日：2007-08-08

  The application describes combinations of at least three amphipatic substances forming aggregate suspensions in a polar liquid. Judicious choice of system components, which differ at least 2-times to 10-times in solubility, ensures said aggregates to have extended, unusually adaptable surfaces. This is probably due to simultaneous action on said aggregates of at least two more soluble substances amongst said three system components, at least one of which is an active ingredient and preferably a drug; the third component, alternatively, can take the role of a drug. The application further deals with the use of said combinations in pharmaceutical preparations capable of transporting drugs into the body of warm blood creatures. This is made possible by the drug loading capability of said aggregates with the highly flexible and deformable coating, which renders the resulting drug carriers highly adaptable. The application finally reveals suitable methods and favourable conditions for carrier manufacturing and application. The application also describes novel formulations of nonsteroidal anti-inflammatory drugs (NSAIDs) based on complex aggregates with at least three amphipatic components suspended in a suitable, e.g. pharmaceutically acceptable, polar liquid medium.

  该申请描述了在极性液体中形成聚集悬浮液的至少三种两性物质的组合。对溶解度至少相差 2 倍到 10 倍的体系成分的明智选择，确保了所述聚集体具有扩展的、异常适应的表面。这可能是由于在上述三种系统成分中，至少有两种可溶性物质同时作用于上述聚集体，其中至少有一种是活性成分，最好是药物；第三种成分也可以起到药物的作用。本申请还涉及上述组合物在药物制剂中的应用，这些药物制剂能够将药物输送到温血动物体内。这得益于具有高柔韧性和可变形涂层的聚合体的药物装载能力，从而使所制成的药物载体具有很强的适应性。该申请最终揭示了载体制造和应用的合适方法和有利条件。本申请还介绍了非甾体抗炎药（NSAIDs）的新型制剂，该制剂基于悬浮在适当的（如药学上可接受的）极性液体介质中的至少含有三种两性成分的复合聚集体。