1-(2'-acetamido-3',4',6'-tri-O-acetyl-2'-deoxy-β-D-glucopyranosyl)-4-phenyl-1,2,3-triazole | 26295-44-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2'-acetamido-3',4',6'-tri-O-acetyl-2'-deoxy-β-D-glucopyranosyl)-4-phenyl-1,2,3-triazole
• 英文别名: 4-phenyl-1-(3,4,6-tri-O-acetyl-2-acetylamino-2-deoxy-β-D-glucopyranosyl)-1,2,3-triazole；1-(2'-acetamido-2'-deoxy-3',4',6'-tri-O-acetyl-β-D-glucopyranosyl)-4-phenyl-1,2,3-triazole；[(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-(4-phenyltriazol-1-yl)oxan-2-yl]methyl acetate
• CAS: 26295-44-3
• 化学式: C₂₂H₂₆N₄O₈
• 分子量: 474.47
• InChiKey: RCEYEYGLTXDPNW-ZGJYDULXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  148
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-(2'-acetamido-3',4',6'-tri-O-acetyl-2'-deoxy-β-D-glucopyranosyl)-4-phenyl-1,2,3-triazole 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以94%的产率得到1-(2'-acetamido-2'-deoxy-β-D-glucopyranosyl)-4-phenyl-1,2,3-triazole
  参考文献：
  名称：

  Design and synthesis of O-GlcNAcase inhibitors via ‘click chemistry’ and biological evaluations

  摘要：

  Protein O-GlcNAcylation has been shown to play an important role in a number of biological processes, including regulation of the cell cycle, DNA transcription and translation, signal transduction, and protein degradation. O-GlcNAcase (OGA) is responsible for the removal of O-linked beta-N-acetylglucosamine (O-GlcNAc) from serine or threonine residues, and thus plays a key role in O-GlcNAc metabolism. Potent OGA inhibitors are useful tools for studying the cellular processes of O-GlcNAc, and may be developed as drugs for the treatment neurodegenerative diseases. In this study, Cu(I)-catalyzed 'Click' cycloaddition reactions between glycosyl azides and alkynes were exploited to generate inhibitory candidates of OGA. Enzymatic kinetic screening revealed that compound 7 was a potent competitive inhibitor of human O-GlcNAcase (K(i) = 185.6 mu M). Molecular docking simulations of compound 7 into CpOGA (Clostridium perfringens OGA) suggested that strong pi-pi stacking interaction between the compound and W490 considerably contributed to improving the inhibitory activity. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.03.026
• 作为产物：
  描述：

  β-D-葡萄糖胺五乙酸酯 在 iron(III) chloride 、 叠氮基三甲基硅烷 、 铜 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 84.0h， 生成 1-(2'-acetamido-3',4',6'-tri-O-acetyl-2'-deoxy-β-D-glucopyranosyl)-4-phenyl-1,2,3-triazole
  参考文献：
  名称：

  Iron(iii) chloride as an efficient catalyst for stereoselective synthesis of glycosyl azides and a cocatalyst with Cu(0) for the subsequent click chemistry

  摘要：

  一种高效而温和的方法被开发出来，利用廉价的FeCl3作为催化剂，实现了糖基β-过乙酸酯的叠氮糖基化反应，制备了1,2-反式糖基叠氮化合物。此外，我们首次证明了FeCl3与铜粉的组合能够促进叠氮糖基与末端炔烃的1,3-偶极环加成反应（点击化学）。在糖基叠氮化和随后的环加成反应过程中，均获得了良好至优异的产率，并且仅形成单一的异构体。

  DOI：

  10.1039/c1cc13370e

文献信息

• Synthesis of Dendritic Glycoclusters and Their Applications for Supramolecular Gelation and Catalysis
  作者：Guijun Wang、Dan Wang、Jonathan Bietsch、Anji Chen、Pooja Sharma

  DOI：10.1021/acs.joc.0c01978

  日期：2020.12.18

  as ligands in copper-catalyzed azide and alkyne cycloaddition (CuAAC) reactions were studied. The compounds with a lower number of branches exhibit excellent gelation properties and can function as supramolecular gelators. The resulting gels were characterized using optical microcopy and atomic force microscopy. The glycoconjugates containing six branches showed significant catalytic activity for copper

  设计，合成和表征了具有三个，四个和六个分支的糖基三唑的糖簇。研究了这些分子的自组装性质及其作为配体在铜催化的叠氮化物和炔烃环加成（CuAAC）反应中的催化活性。具有较低支链数的化合物表现出优异的胶凝特性，并且可以用作超分子胶凝剂。使用光学显微镜和原子力显微镜对所得的凝胶进行表征。含有六个分支的糖缀合物对硫酸铜介导的环加成反应显示出显着的催化活性。在水溶液中，至底物的1mol％糖簇有效地促进了这些反应。发现几种三聚化合物能够与催化活性六聚化合物形成共凝胶。使用由糖缀合物形成的有机凝胶作为超分子催化剂，证明了对几种CuAAC反应的有效催化作用。CuSO金属盐还制备了4个凝胶柱，可重复使用几次以进行环加成反应。这些包括制备一些糖基三唑，芳基三唑和异恶唑。我们期望这些基于糖的软生物材料将具有超分子催化以外的铜催化环加成反应的应用。它们也可用作其他金属离子催化的有机反应的配体或凝胶基质。
• Synthesis of Carbohydrate Based Macrolactones and Their Applications as Receptors for Ion Recognition and Catalysis
  作者：Surya B. Adhikari、Anji Chen、Guijun Wang

  DOI：10.3390/molecules26113394

  日期：——

  cyclization of functionalized D-glucosamine derivatives. These novel macrolactones have unique structures and demonstrate interesting anion binding properties, especially for chloride. The macrocycles containing two triazoles form complexes with copper sulfate, and they are effective ligands for copper sulfate mediated azide-alkyne cycloaddition reactions (CuAAC). In addition, several macrocycles show

  聚糖大内酯表现出许多有趣的生物学特性，它们在分子识别和超分子化学中也很重要。因此，能够获得具有不同尺寸和功能的糖大环非常重要。设计并合成了一系列新的含有三唑和内酯部分的基于碳水化合物的大环化合物。该合成以大环化步骤的分子内亲核取代反应为特征。在本文中，评估了一些常见磺酸盐离去基团对大内酯化的影响。使用甲苯磺酸酯对单内酯化产物具有良好的选择性和良好的产率。已经合成并表征了14个不同的大环，其中11个大环来自N-乙酰基D-葡糖胺衍生物的C1至C6位置的环化，另外3个大环来自官能化的D-葡糖胺衍生物的C2至C6环化。这些新型大环内酯具有独特的结构，并表现出有趣的阴离子结合特性，特别是对于氯离子。含有两个三唑的大环与硫酸铜形成配合物，它们是硫酸铜介导的叠氮-炔环加成反应（CuAAC）的有效配体。此外，一些大环化合物对不同的炔烃表现出一定的选择性。
• Syntheses of <i>Bis</i> ‐Triazole Linked Carbohydrate Based Macrocycles and Their Applications for Accelerating Copper Sulfate Mediated Click Reaction
  作者：Anji Chen、Lalith P. Samankumara、Sanjeeva Dodlapati、Dan Wang、Surya Adhikari、Guijun Wang

  DOI：10.1002/ejoc.201801714

  日期：2019.2.14

  Eight glucosamine based 1,2,3‐triazole linked macrocycles were synthesized starting from the readily available N‐acetyl‐d‐glucosamine. These bis‐triazole‐linked glycomacrocycles showed remarkable rate acceleration for CuSO4 mediated azide and alkyne cycloaddition reactions in aqueous solutions.

  八个葡糖胺基于1,2,3-三唑连接的大环化合物合成从容易获得的起始N-乙酰基- d -葡糖胺。这些双三唑连接的糖大环化合物在水溶液中对CuSO 4介导的叠氮化物和炔烃环加成反应显示出显着的速率加速。
• Synthesis and study of N-acetyl d-glucosamine triazole derivatives as effective low molecular weight gelators
  作者：Hari P.R. Mangunuru、Jayasudhan Reddy Yerabolu、Guijun Wang

  DOI：10.1016/j.tetlet.2015.02.123

  日期：2015.6

  Sugar based low molecular weight gelators have many potential uses for the formation of advanced soft materials. Here we have synthesized a series of peracetylated D-glucosamine triazole derivatives via the Cu catalyzed azide/alkyne cycloaddition reaction (CuAAc) and studied their self-assembling properties in several organic solvents, aqueous solutions, and water. Among the sixteen compounds synthesized and studied, many were able to function as organogelators for multiple solvents. Also seven compounds were able to form hydrogels at low concentrations such as 0.2-1.0 wt %. These indicate that peracetylated D-glucosamine triazole analogs are effective small molecular gelators. (C) 2015 Elsevier Ltd. All rights reserved.
• Evaluation of bis-triphenylphosphano-copper(I)-butyrate (C3H7COOCu(PPh3)2) as catalyst for the synthesis of 1-glycopyranosyl-4-substituted-1,2,3-triazoles
  作者：Éva Bokor、Csenge Koppány、Zsombor Gonda、Zoltán Novák、László Somsák

  DOI：10.1016/j.carres.2012.01.004

  日期：2012.4

  Bis-triphenylphosphano-copper(I)-butyrate (C3H7COOCu(PPh3)(2)) was applied for the synthesis of O-peracylated 1-glycopyranosyl-4-substituted-1,2,3-triazoles from the corresponding glycosyl azides and alkynes. This catalyst proved superior to the CuSO4/L-ascorbic acid system even with sterically hindered and less reactive glycosyl azides. (C) 2012 Elsevier Ltd. All rights reserved.