(2R,3R,4S,5R,6R)-2-(4-((dodecyloxy)methyl)-1H-1,2,3-triazol-1-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol | 1083009-15-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R,6R)-2-(4-((dodecyloxy)methyl)-1H-1,2,3-triazol-1-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
• 英文别名: 4-(dodecyloxymethyl)-1-(β-D-galactopyranosyl)-1H-[*1,2,3]triazole
• CAS: 1083009-15-7
• 化学式: C₂₁H₃₉N₃O₆
• 分子量: 429.557
• InChiKey: FKTZDJXWIOHTJY-XDWAVFMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.69
• 重原子数：
  30.0
• 可旋转键数：
  15.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  130.09
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  4-(dodecyloxymethyl)-1-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-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(2R,3R,4S,5R,6R)-2-(4-((dodecyloxy)methyl)-1H-1,2,3-triazol-1-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
  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

• 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.