6-azidohexyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 382146-72-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-azidohexyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: I(2)-D-Glucopyranoside, 6-azidohexyl, 2,3,4,6-tetraacetate；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(6-azidohexoxy)oxan-2-yl]methyl acetate
• CAS: 382146-72-7
• 化学式: C₂₀H₃₁N₃O₁₀
• 分子量: 473.48
• InChiKey: SKIIWRPBHDLTRM-OUUBHVDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.96
• 重原子数：
  33.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  172.42
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  6-azidohexyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 5%-palladium/activated carbon 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 6-N-(tert-butyloxycarbonyl)hexyl β-D-glucopyranoside
  参考文献：
  名称：

  碳水化合物作为多价免疫原的潜在多功能核心子载体。

  摘要：

  携带碳水化合物抗原表位的合成多价糖簇已被认为是开发碳水化合物疫苗的有希望的候选者。在这里，我们描述了一种使用糖作为多功能核心子载体来合成缀合就绪多价糖簇的收敛策略。D-葡萄糖和龙胆二糖被转化为聚炔官能化核心，然后使用点击化学用带有叠氮化物的模型配体D-葡萄糖装饰，形成结构明确的四价和七价糖簇。通过方酸化学将每个簇与模型蛋白牛血清白蛋白 (BSA) 缀合。通过改变核心的结构和构型，可以制备各种尺寸和空间排列的碳水化合物簇，具体取决于用于其组装的单糖或寡糖。建议使用碳水化合物作为核心副载体提供了定制抗原的大小和拓扑并以优化簇效应以获得更强的免疫反应性的方式修改免疫原的多价呈递的机会。

  DOI：

  10.1039/c6ra27181b
• 作为产物：
  描述：

  (6-hydroxyhexyl)tosylate 在 sodium azide 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 6-azidohexyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Click reaction based synthesis, antimicrobial, and cytotoxic activities of new 1,2,3-triazoles

  摘要：

  Three-motif pharmacophoric models 20a-e and 21-25 were prepared in good yields by CuAAC of two azido substrates 2 and 11 with seven terminal acetylenic derivatives including chalcones 17a-e, theophylline 18 and cholesterol 19. The structure of these compounds was elucidated by NMR, MS, IR spectroscopy and micro analyses. This series was screened as antimicrobial and cytotoxic agents in vitro. Most derivatives showed appreciable antibacterial activity, but they displayed weak cytotoxic, and antifungal activities. Notably, conjugate 25 (cream of the crop) was found to be more active than Ampicillin against Escherichia coli and Staphylococcus aureus and showed appreciable antifungal and cytotoxic activities as well. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.04.096

文献信息

• Synthesis of β-1,3-glucan mimics by β-1,3-glucan trisaccharyl monomer polymerization
  作者：Atsushi Miyagawa、Hatsuo Yamamura

  DOI：10.1016/j.carbpol.2019.115105

  日期：2020.1

  monomers were separated by silica gel chromatography and identified by NMR spectroscopy and mass spectrometry. The synthesized glycosyl monomers were polymerized and copolymerized with norbornene using 2nd generation Hoveyda-Grubbs catalyst, deprotected, and purified by gel filtration to prepare water-soluble glycopolymers of varied compositions and high molecular weights. These polymers will have the

  β-1，3-葡聚糖在活生物体中作为免疫刺激剂很重要。β-1,3-葡聚糖与细胞表面受体dectin-1的多价结合可激活免疫防御。为了研究人工免疫刺激剂，合成了以β-1,3-葡聚糖三糖为人工配体的糖聚合物。由D-葡萄糖通过糖基化作用构建了定义为β-1,3-葡聚糖活性单元的β-1,3-葡聚糖三糖。将降冰片烯基团作为可聚合基团引入糖苷配基的三糖衍生物中。准备的内/外通过硅胶色谱分离单体的降冰片烯立体异构体，并通过NMR光谱和质谱鉴定。使用第二代Hoveyda-Grubbs催化剂将合成的糖基单体与降冰片烯聚合并共聚，脱保护，并通过凝胶过滤纯化，以制备具有不同组成和高分子量的水溶性糖聚合物。这些聚合物具有与dectin-1多价结合以激活免疫反应的潜力，并有助于研究以了解β-1,3-葡聚糖与dectin-1的结合机制。
• 一类具有环状结构的蒽醌糖缀合物及其制备 方法和在环境检测中的应用
  申请人：河南师范大学

  公开号：CN106928295B

  公开（公告）日：2019-10-11

  本发明公开了一类具有环状结构的蒽醌糖缀合物及其制备方法和在环境检测中的应用，属于药物中间体及荧光探针分子的合成技术领域。本发明的技术方案要点为：本发明操作简便，反应条件温和，所用试剂均为工业常用试剂，适合大量工业化制备；合成路线简洁，通过更改一些单糖即可发散式获得大量的具有环状结构的蒽醌糖缀合物，并对其进行荧光活性测试，结果显示该具有环状结构的蒽醌糖缀合物能够较好地应用于环境中重金属离子的检测。
• Sonochemistry:  A Powerful Way of Enhancing the Efficiency of Carbohydrate Synthesis
  作者：Shenglou Deng、Umesh Gangadharmath、Cheng-Wei Tom Chang

  DOI：10.1021/jo060374w

  日期：2006.7.1

  [GRAPHICS]Using sonication as a means of facilitating organic reactions in carbohydrate chemistry was explored under the conditions used for traditional organic synthesis. An array of representative reactions, including hydroxy group manipulation ( acylation, protection/deprotection, acyl group migration), thioglycoside synthesis, azidoglycoside synthesis, 1,3-dipolar cycloaddition and reductive cleavage of benzylidene, commonly used in the synthesis of carbohydrate derivatives was examined. A series of glycosylation reactions that employ thioglycosides, glycosyl trichloroacetimidate, glycosyl bromide and glycosyl acetate as the glycosyl donors was also examined. Our results demonstrate that sonication can significantly shorten the reaction time, enhance the reactivity of reactant and lead to superior yield and excellent stereoselectivity. More importantly, a general protocol of glycosylation may finally be developed. Sonication is compatible to the conditions used for traditional organic synthesis. We believe that sonication can also be applied to other areas of synthetic processes.