6-deoxy-1,2:3,4-di-O-isopropylidene-6-(4-phenyl-1H-1,2,3-triazol-1-yl)-α-D-galactopyranose | 34279-98-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-deoxy-1,2:3,4-di-O-isopropylidene-6-(4-phenyl-1H-1,2,3-triazol-1-yl)-α-D-galactopyranose
• 英文别名: 1,2:3,4-di-O-isopropylidene-6-(4-phenyl-1H-1,2,3-triazol-1-yl)-α-D-galactopyranose；O¹,O²;O³,O⁴-diisopropylidene-6-(4-phenyl-[1,2,3]triazol-1-yl)-α-D-6-deoxy-galactopyranose；4-phenyl-1-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methyl]triazole
• CAS: 34279-98-6
• 化学式: C₂₀H₂₅N₃O₅
• 分子量: 387.436
• InChiKey: SFSRPJYHZVXFPW-DISONHOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  76.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  6-azido-6-deoxy-1,2:3,4-di-O-isopropylidene-D-galactopyranose 、 苯乙炔 在 copper(l) iodide 作用下， 以95%的产率得到6-deoxy-1,2:3,4-di-O-isopropylidene-6-(4-phenyl-1H-1,2,3-triazol-1-yl)-α-D-galactopyranose
  参考文献：
  名称：

  无胺条件下离子液体中铜（I）催化的叠氮化物-炔烃环加成反应

  摘要：

  在不添加游离胺的情况下，在市售的多氧化离子液体（AMMOENG 100™）中进行结构多样的有机叠氮化物和末端炔烃的各种组合的碘化亚铜（I）催化的环加成反应。与先前测试过的离子液体不同，该溶剂仅产生1,4-二取代的三唑区域异构体。 炔烃-叠氮化物-碳水化合物-铜-环加成

  DOI：

  10.1055/s-0029-1218760

文献信息

• Organocatalyzed Regioselective Synthesis of 1,5‐Disubstituted 1,2,3‐Triazolyl Glycoconjugates
  作者：Manoj K. Jaiswal、Abhishek Gupta、Mangal S. Yadav、Vinay K. Pandey、Vinod K. Tiwari

  DOI：10.1002/chem.202301749

  日期：2023.10.2

  A novel route using Schreiner thiourea mediated organocatalyzed [3+2] cycloaddition reaction of nitroolefins with diverse azides is devised to furnish high yield of 1,5-disubstituted 1,2,3-triazolyl glycoconjugates. The method has some notable features including metal-free, straightforward, acid-free, excellent regioselectivity operationally simple, wide substrate scope and high yielding. The Schreiner

  设计了一种使用 Schreiner 硫脲介导的硝基烯烃与多种叠氮化物的有机催化 [3+2] 环加成反应的新路线，以提供高产率的 1,5-二取代 1,2,3-三唑基糖缀合物。该方法具有无金属、简单、无酸、区域选择性好、操作简单、底物范围广、产率高等显着特点。Schreiner 硫脲有机催化剂能够通过双氢键实现硝基烯烃所需的活化。
• Synthesis, Biological Activity, and Molecular Modeling Studies of 1<i>H</i>-1,2,3-Triazole Derivatives of Carbohydrates as α-Glucosidases Inhibitors
  作者：Sabrina B. Ferreira、Ana C. R. Sodero、Mariana F. C. Cardoso、Emerson S. Lima、Carlos R. Kaiser、Floriano P. Silva、Vitor F. Ferreira

  DOI：10.1021/jm901265h

  日期：2010.3.25

  A class of drugs in use for treating type II diabetes mellitus (T2D), typified by the pseudotetrasaccharide acarbose, act by inhibiting the a-glucosidase activity present in pancreatic secretions and in the brush border of the small intestine. Herein, we report the synthesis of a series of 4-substituted 1,2,3-triazoles conjugated with sugars, including D-xylose, D-galactose, D-allose, and D-ribose. Compounds were screened for alpha-glucosidase inhibitory activity using yeast maltase (MAL12) as a model enzyme. Methyl-2,3-O-isopropylidene-beta-D-riboluranosides, such as the 4-(1-cyclohexenyl)-1,2,3-triazole derivative, were among the most active compounds, showing up to 25-fold higher inhibitory potency than the complex oligosaccharide acarbose. Docking studies on a MAL12 homology model disclosed a binding mode consistent with a transition-state-mimicking mechanism. Finally, the actual pharmacological potential of this triazole series was demonstrated by the reduction of postprandial blood glucose levels in normal rats. These compounds could represent new chemical scaffolds for developing novel drugs against T2D.