4-(dodecyloxymethyl)-1-(β-D-glucopyranosyl)-1H-[*1,2,3]triazole | 1083009-13-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(dodecyloxymethyl)-1-(β-D-glucopyranosyl)-1H-[*1,2,3]triazole
• 英文别名: (2R,3R,4S,5S,6R)-2-[4-(dodecoxymethyl)triazol-1-yl]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1083009-13-5
• 化学式: C₂₁H₃₉N₃O₆
• 分子量: 429.557
• InChiKey: FKTZDJXWIOHTJY-YMQHIKHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  30
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  130
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-(dodecyloxymethyl)-1-(β-D-glucopyranosyl)-1H-[*1,2,3]triazole 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydride 、 乙酰氯 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 9.0h， 生成
  参考文献：
  名称：

  Research on the structure–surface adsorptive activity relationships of triazolyl glycolipid derivatives for mild steel in HCl

  摘要：

  Triazolyl glycolipid derivatives constructed via CuI-catalyzed azide-alkyne 1,3-dipolar cycloaddition reaction (Cue-AAC) represent a new range of carbohydrate-based scaffolds for use in many fields of the chemical research. Here the surface adsorptive ability of series of our previously prepared C1- or C6-triazole linked gluco-and galactolipid derivatives for mild steel in 1 M HCl was studied via electrochemical impedance spectroscopy (EIS). Results indicated that these monosaccharide-fatty acid conjugates are weak inhibitors against HCl corrosion for mild steel. Moreover, some newly synthesized triazolyl disaccharide (maltose)-fatty alcohol conjugates failed to display enhanced activity, meaning that the structural enlargement of the sugar moiety does not favor the iron surface adsorption. However, a bistriazolyl glycolipid derivative, which was realized by introducing a benzenesulfonamide group via Cue-AAC to the C6-position of a C1-triazolyl glucolipid analog, eventually showed significantly improved adsorptive potency compared to that of its former counterparts. The corrosion inhibitive modality of this compound for mild steel in HCl was subsequently studied via potentiodynamic polarization and thermodynamic calculations. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.03.006
• 作为产物：
  描述：

  4-(dodecyloxymethyl)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-1H-[*1,2,3]triazole 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以99%的产率得到4-(dodecyloxymethyl)-1-(β-D-glucopyranosyl)-1H-[*1,2,3]triazole
  参考文献：
  名称：

  使用离子液体作为双促进剂 - 溶剂方便合成长烷基链三唑基糖苷：易于获得非离子三唑基糖苷表面活性剂以评估细胞毒活性

  摘要：

  通过连续的一锅两步糖苷化-CuAAc点击反应，描述了一种使用离子液体作为双促进剂和溶剂一锅合成长烷基链三唑基糖苷的简便方法。该反应使用市售的底物进行，包括糖基溴化物、叠氮化钠和各种长烷基链炔烃，以中等至高产率获得相应的产物。此外，该方法通过简单的脱乙酰作用以优异的产率成功地应用于制备非离子单链三唑基糖苷表面活性剂。随后，进一步评估了这些表面活性剂的细胞毒活性。

  DOI：

  10.1016/j.tetlet.2021.153325

文献信息

• 三氮唑糖脂类衍生物及其协同抗耐药菌的用 途
  申请人：华东理工大学

  公开号：CN104530163B

  公开（公告）日：2017-08-22

  本发明涉及一种含单糖基团的三氮唑衍生物及其用途，所述含单糖基团的三氮唑衍生物，为式Ⅰ所示化合物，或其在药学上可接受的盐。本发明提供的三氮唑衍生物对现有抗生素的抑菌具有增效作用，其与现有抗生素联合使用，可大大降低抗生素用量，为合理安全使用抗生素提供了一种途径。式Ⅰ中，R1为有乙酰基保护或没有乙酰基保护的单糖基团；R2为C6～C18直链或支链的烷基；n为1～4的整数。
• Synthesis of novel glycolipids derived from glycopyranosyl azides and N-(β-glycopyranosyl)azidoacetamides
  作者：Katuri J.V. Paul、Duraikkannu Loganathan

  DOI：10.1016/j.tetlet.2008.08.073

  日期：2008.10

  A general and expedient method based on a click reaction has been developed for the synthesis of novel glycolipids. The Cu(I) catalyzed [3+2] cycloaddition of several fully acetylated beta- as well as alpha-D-glycopyranosyl azides, including the 1,6-diazide derived from D-glucose, with long chain alkyl propargyl ethers gave the respective 1,4-substituted 1,2,3-triazole derivatives in good yields. Treatment of fully acetylated N-(beta-glycopyranosyl)azidoacetamides under similar conditions with alkyl propargyl ethers afforded the 1,2,3-triazolylacetamido derivatives in fairly good yields. Zemplen de-O-acetylation of all the fully acetylated derivatives furnished the free glycolipids in quantitative yields. (c) 2008 Elsevier Ltd. All rights reserved.
• Triazole-Linked Glycolipids Enhance the Susceptibility of MRSA to β-Lactam Antibiotics
  作者：Xi-Le Hu、Dan Li、Lei Shao、Xiaojing Dong、Xiao-Peng He、Guo-Rong Chen、Daijie Chen

  DOI：10.1021/acsmedchemlett.5b00142

  日期：2015.7.9

  We show here that a series of triazolyl glycolipid derivatives modularly synthesized by a "click" reaction have the ability to increase the susceptibility of a drug-resistant bacterium to beta-lactam antibiotics. We determine that the glycolipids can suppress the minimal inhibitory concentration of a number of ineffective beta-lactams, upward of 256-fold, for methicillin-resistant Staphylococuss aureus (MRSA). The mechanism of action has been preliminarily probed and discussed.
• Convenient synthesis of long alkyl-chain triazolylglycosides using ionic liquid as dual promoter-solvent: Readily access to non-ionic triazolylglycoside surfactants for evaluation of cytotoxic activity
  作者：Nutthanicha Ketsomboon、Rungnapha Saeeng、Klaokwan Srisook、Uthaiwan Sirion

  DOI：10.1016/j.tetlet.2021.153325

  日期：2021.9

  one-pot synthesis of long alkyl-chain triazolylglycosides using ionic liquid as dual promoter and solvent is described via a sequential one-pot two-step glycosidation-CuAAc click reaction. The reaction was carried out using commercially available substrates, including glycosyl bromides, sodium azide and various long alkyl-chain alkynes to achieve the corresponding products in moderate to high yields

  通过连续的一锅两步糖苷化-CuAAc点击反应，描述了一种使用离子液体作为双促进剂和溶剂一锅合成长烷基链三唑基糖苷的简便方法。该反应使用市售的底物进行，包括糖基溴化物、叠氮化钠和各种长烷基链炔烃，以中等至高产率获得相应的产物。此外，该方法通过简单的脱乙酰作用以优异的产率成功地应用于制备非离子单链三唑基糖苷表面活性剂。随后，进一步评估了这些表面活性剂的细胞毒活性。
• Research on the structure–surface adsorptive activity relationships of triazolyl glycolipid derivatives for mild steel in HCl
  作者：Hai-Lin Zhang、Xiao-Peng He、Qiong Deng、Yi-Tao Long、Guo-Rong Chen、Kaixian Chen

  DOI：10.1016/j.carres.2012.03.006

  日期：2012.6

  Triazolyl glycolipid derivatives constructed via CuI-catalyzed azide-alkyne 1,3-dipolar cycloaddition reaction (Cue-AAC) represent a new range of carbohydrate-based scaffolds for use in many fields of the chemical research. Here the surface adsorptive ability of series of our previously prepared C1- or C6-triazole linked gluco-and galactolipid derivatives for mild steel in 1 M HCl was studied via electrochemical impedance spectroscopy (EIS). Results indicated that these monosaccharide-fatty acid conjugates are weak inhibitors against HCl corrosion for mild steel. Moreover, some newly synthesized triazolyl disaccharide (maltose)-fatty alcohol conjugates failed to display enhanced activity, meaning that the structural enlargement of the sugar moiety does not favor the iron surface adsorption. However, a bistriazolyl glycolipid derivative, which was realized by introducing a benzenesulfonamide group via Cue-AAC to the C6-position of a C1-triazolyl glucolipid analog, eventually showed significantly improved adsorptive potency compared to that of its former counterparts. The corrosion inhibitive modality of this compound for mild steel in HCl was subsequently studied via potentiodynamic polarization and thermodynamic calculations. (C) 2012 Elsevier Ltd. All rights reserved.