[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-[4-(octoxymethyl)triazol-1-yl]oxan-2-yl]methyl acetate | 1083009-00-0

• 英文名称: [(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-[4-(octoxymethyl)triazol-1-yl]oxan-2-yl]methyl acetate
• CAS: 1083009-00-0
• 化学式: C₂₅H₃₉N₃O₁₀
• 分子量: 541.599
• InChiKey: PXVXVJXKWQBYEL-WJGLBBAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  38
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  154
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-[4-(octoxymethyl)triazol-1-yl]oxan-2-yl]methyl acetate 在 甲醇 、 sodium methylate 作用下， 以100%的产率得到(2R,3S,4S,5S,6R)-2-(hydroxymethyl)-6-(4-((octyloxy)methyl)-1H-1,2,3-triazol-1-yl)tetrahydro-2H-pyran-3,4,5-triol
  参考文献：
  名称：

  Synthesis of novel glycolipids derived from glycopyranosyl azides and N-(β-glycopyranosyl)azidoacetamides

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2008.08.073
• 作为产物：
  描述：

  2-(乙酰氧基甲基)-6-叠氮基四氢-2H-吡喃-3,4,5-三基三乙酸酯 、 正辛基炔丙基醚 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 12.0h， 以87%的产率得到[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-[4-(octoxymethyl)triazol-1-yl]oxan-2-yl]methyl acetate
  参考文献：
  名称：

  Triazole-Linked Glycolipids Enhance the Susceptibility of MRSA to β-Lactam Antibiotics

  摘要：

  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.

  DOI：

  10.1021/acsmedchemlett.5b00142