2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-β-D-glucofurano)[2,1-d]-2-oxazoline

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-β-D-glucofurano)[2,1-d]-2-oxazoline
• 英文别名: (3aR,5S,6R,6aR)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methyl-3a,5,6,6a-tetrahydrofuro[3,2-d][1,3]oxazol-6-ol
• 化学式: C₁₁H₁₇NO₅
• 分子量: 243.26
• InChiKey: BLASPHDBCPYTRC-CHHOWFRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  69.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-β-D-glucofurano)[2,1-d]-2-oxazoline 在 camphor-10-sulfonic acid 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 methyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside
  参考文献：
  名称：

  作为登革热病毒拮抗剂的高效合成的Muramic和葡萄糖醛酸Glycodendrimers。

  摘要：

  碳水化合物通过糖-蛋白相互作用参与许多重要的病理过程，例如细菌和病毒感染。具有多种碳水化合物的糖缀合物参与多价相互作用，因此增加了它们与蛋白质的结合强度。在这项工作中，我们报告了新型的山武和葡萄糖醛酸糖树状聚合物作为潜在的登革热病毒拮抗剂的有效合成。通过点击化学，通过优化的合成策略，通过点击化学将具有末端乙炔基官能化的芳族支架偶联至村族和葡糖醛酸叠氮化物，从而以高收率提供所需的糖类树状聚合物。表面等离子体共振研究表明，所报道的化合物与登革热病毒包膜蛋白有效结合。进行了分子建模研究以模拟和解释观察到的结合。这些研究证实，可以轻松地实现糖类树状聚合物的有效化学合成，从而为寻找针对登革热病毒的新活性化合物提供了一种通用的策略。

  DOI：

  10.1002/chem.201903788
• 作为产物：
  描述：

  D-GlcNAc 、 丙酮 在 三氯化铁 作用下， 反应 0.33h， 以71%的产率得到2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-β-D-glucofurano)[2,1-d]-2-oxazoline
  参考文献：
  名称：

  An inexpensive fluorescent labeling protocol for bioactive natural products utilizing Cu(I)-catalyzed Huisgen reaction

  摘要：

  Labeling of bioactive small molecules with organic dyes for various applications in cell biology has been emerging as an attractive research field. Using an easily prepared and inexpensive fluorescein derivative 1 and a Cu(I)-catalyzed Huisgen reaction, an efficient fluorescent labeling strategy is developed generally for bioactive natural products. Essentials of a successful labeling include the personalized introduction of an azido functionality to specific targets by a selective and efficient manner, and the strategic adjustment of reaction sequence to avoid possible side reactions under the 'click' reaction conditions. Such a protocol has been successfully applied to the fluorescent labeling of four bioactive small molecules in different chemical categories in this study. Advantages of this labeling protocol include the use of inexpensive reagents, ease of operation, free-of-protections at the 'click' step, and suiting a wide range of bioactive molecules bearing the reactive functionalities. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.069

文献信息

• Efficient Synthesis of Muramic and Glucuronic Acid Glycodendrimers as Dengue Virus Antagonists
  作者：Cecilia García‐Oliva、Alfredo H. Cabanillas、Almudena Perona、Pilar Hoyos、Ángel Rumbero、María J. Hernáiz

  DOI：10.1002/chem.201903788

  日期：2020.2.3

  interactions, thus increasing their binding strengths to proteins. In this work, we report the efficient synthesis of novel muramic and glucuronic acid glycodendrimers as potential Dengue virus antagonists. Aromatic scaffolds functionalized with a terminal ethynyl groups were coupled to muramic and glucuronic acid azides by click chemistry through optimized synthetic strategies to afford the desired glycodendrimers

  碳水化合物通过糖-蛋白相互作用参与许多重要的病理过程，例如细菌和病毒感染。具有多种碳水化合物的糖缀合物参与多价相互作用，因此增加了它们与蛋白质的结合强度。在这项工作中，我们报告了新型的山武和葡萄糖醛酸糖树状聚合物作为潜在的登革热病毒拮抗剂的有效合成。通过点击化学，通过优化的合成策略，通过点击化学将具有末端乙炔基官能化的芳族支架偶联至村族和葡糖醛酸叠氮化物，从而以高收率提供所需的糖类树状聚合物。表面等离子体共振研究表明，所报道的化合物与登革热病毒包膜蛋白有效结合。进行了分子建模研究以模拟和解释观察到的结合。这些研究证实，可以轻松地实现糖类树状聚合物的有效化学合成，从而为寻找针对登革热病毒的新活性化合物提供了一种通用的策略。
• An inexpensive fluorescent labeling protocol for bioactive natural products utilizing Cu(I)-catalyzed Huisgen reaction
  作者：Yan-Hong Zhang、Zheng-Xi Gao、Chun-Long Zhong、Hai-Bin Zhou、Lei Chen、Wen-Min Wu、Xin-Jun Peng、Zhu-Jun Yao

  DOI：10.1016/j.tet.2007.04.069

  日期：2007.7

  Labeling of bioactive small molecules with organic dyes for various applications in cell biology has been emerging as an attractive research field. Using an easily prepared and inexpensive fluorescein derivative 1 and a Cu(I)-catalyzed Huisgen reaction, an efficient fluorescent labeling strategy is developed generally for bioactive natural products. Essentials of a successful labeling include the personalized introduction of an azido functionality to specific targets by a selective and efficient manner, and the strategic adjustment of reaction sequence to avoid possible side reactions under the 'click' reaction conditions. Such a protocol has been successfully applied to the fluorescent labeling of four bioactive small molecules in different chemical categories in this study. Advantages of this labeling protocol include the use of inexpensive reagents, ease of operation, free-of-protections at the 'click' step, and suiting a wide range of bioactive molecules bearing the reactive functionalities. (c) 2007 Elsevier Ltd. All rights reserved.