(R)-2-(((4aR,6R,7R,8R,8aS)-7-acetamido-6-((10-azidodecyl)oxy)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)propanoic acid | 945761-19-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: (R)-2-(((4aR,6R,7R,8R,8aS)-7-acetamido-6-((10-azidodecyl)oxy)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)propanoic acid
• CAS: 945761-19-3
• 化学式: C₂₄H₄₂N₄O₈
• 分子量: 514.619
• InChiKey: AYDJAHJVYUQLHX-AGZOZPPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  36.0
• 可旋转键数：
  16.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  161.31
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (R)-2-(((4aR,6R,7R,8R,8aS)-7-acetamido-6-((10-azidodecyl)oxy)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)propanoic acid 在 copper(l) iodide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 52.0h， 生成 (4S)-4-[[(2S)-2-[[(2R)-2-[[(4aR,6R,7R,8R,8aS)-7-acetamido-6-[10-[4-[(6'-hydroxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-3'-yl)oxymethyl]triazol-1-yl]decoxy]-2,2-dimethyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]propanoyl]amino]propanoyl]amino]-5-amino-5-oxopentanoic acid
  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
• 作为产物：
  描述：

  2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-β-D-glucofurano)[2,1-d]-2-oxazoline 在 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 (R)-2-(((4aR,6R,7R,8R,8aS)-7-acetamido-6-((10-azidodecyl)oxy)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)propanoic acid
  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