7-hydroxy-3-[4-[[(2R,3R,4S,5R,6S)-3-[[1-(7-hydroxy-2-oxochromen-3-yl)triazol-4-yl]methoxy]-6-methoxy-4,5-bis(phenylmethoxy)oxan-2-yl]methoxymethyl]triazol-1-yl]chromen-2-one | 1415679-80-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-hydroxy-3-[4-[[(2R,3R,4S,5R,6S)-3-[[1-(7-hydroxy-2-oxochromen-3-yl)triazol-4-yl]methoxy]-6-methoxy-4,5-bis(phenylmethoxy)oxan-2-yl]methoxymethyl]triazol-1-yl]chromen-2-one
• CAS: 1415679-80-9
• 化学式: C₄₅H₄₀N₆O₁₂
• 分子量: 856.846
• InChiKey: SBVGJNCKDGTFRV-PGHZTTKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  63
• 可旋转键数：
  16
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  210
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  7-hydroxy-3-[4-[[(2R,3R,4S,5R,6S)-3-[[1-(7-hydroxy-2-oxochromen-3-yl)triazol-4-yl]methoxy]-6-methoxy-4,5-bis(phenylmethoxy)oxan-2-yl]methoxymethyl]triazol-1-yl]chromen-2-one 在 氢气 、 palladium dichloride 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以96.3%的产率得到3-(4-((((2R,3S,4R,5R,6S)-4,5-dihydroxy-2-(((1-(7-hydroxy-2-oxo-2H-chromen-3-yl)-1H-1,2,3-triazol-4-yl)methoxy)methyl)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)methyl)-1H-1,2,3-triazol-1-yl)-7-hydroxy-2H-chromen-2-one
  参考文献：
  名称：

  Construction of triazolyl bidentate glycoligands (TBGs) by grafting of 3-azidocoumarin to epimeric pyranoglycosides via a fluorogenic dual click reaction

  摘要：

  Glycoligands, which feature a glycoside as the central template incorporating Lewis bases as metal chelation sites and various fluorophores as the chemical reporter, represent a range of interesting scaffolds for development of chemosensors. Here, new types of triazolyl bidentate glycoligands (TBGs) based on the grafting of 3-azidocoumarin to the C2,3- or C4,6-positions of three epimeric pyranoglycosides including a glucoside, a galactoside, and a mannoside were efficiently synthesized via a fluorogenic dual click reaction assisted by microwave irradiation. The desired TBGs were afforded in high conversion rates (>90%) and reasonable yields (similar to 70%). Moreover, a preliminary optical study of two hydroxyl-free glucoside-based TBGs indicates that these compounds are strongly fluorescent in pure water, implying their potential for ion detections in aqueous media. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.10.001
• 作为产物：
  描述：

  methyl 2,3-di-O-benzyl-4,6-di-O-propargyl-α-D-glucopyranoside 、 3-叠氮基-7-羟基氧杂萘邻酮 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 4.0h， 以70.2%的产率得到7-hydroxy-3-[4-[[(2R,3R,4S,5R,6S)-3-[[1-(7-hydroxy-2-oxochromen-3-yl)triazol-4-yl]methoxy]-6-methoxy-4,5-bis(phenylmethoxy)oxan-2-yl]methoxymethyl]triazol-1-yl]chromen-2-one
  参考文献：
  名称：

  Construction of triazolyl bidentate glycoligands (TBGs) by grafting of 3-azidocoumarin to epimeric pyranoglycosides via a fluorogenic dual click reaction

  摘要：

  Glycoligands, which feature a glycoside as the central template incorporating Lewis bases as metal chelation sites and various fluorophores as the chemical reporter, represent a range of interesting scaffolds for development of chemosensors. Here, new types of triazolyl bidentate glycoligands (TBGs) based on the grafting of 3-azidocoumarin to the C2,3- or C4,6-positions of three epimeric pyranoglycosides including a glucoside, a galactoside, and a mannoside were efficiently synthesized via a fluorogenic dual click reaction assisted by microwave irradiation. The desired TBGs were afforded in high conversion rates (>90%) and reasonable yields (similar to 70%). Moreover, a preliminary optical study of two hydroxyl-free glucoside-based TBGs indicates that these compounds are strongly fluorescent in pure water, implying their potential for ion detections in aqueous media. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.10.001

文献信息

• Construction of triazolyl bidentate glycoligands (TBGs) by grafting of 3-azidocoumarin to epimeric pyranoglycosides via a fluorogenic dual click reaction
  作者：Jia-Lu Xue、Xiao-Peng He、Jin-Wei Yang、De-Tai Shi、Chao-Ying Cheng、Juan Xie、Guo-Rong Chen、Kaixian Chen

  DOI：10.1016/j.carres.2012.10.001

  日期：2012.12

  Glycoligands, which feature a glycoside as the central template incorporating Lewis bases as metal chelation sites and various fluorophores as the chemical reporter, represent a range of interesting scaffolds for development of chemosensors. Here, new types of triazolyl bidentate glycoligands (TBGs) based on the grafting of 3-azidocoumarin to the C2,3- or C4,6-positions of three epimeric pyranoglycosides including a glucoside, a galactoside, and a mannoside were efficiently synthesized via a fluorogenic dual click reaction assisted by microwave irradiation. The desired TBGs were afforded in high conversion rates (>90%) and reasonable yields (similar to 70%). Moreover, a preliminary optical study of two hydroxyl-free glucoside-based TBGs indicates that these compounds are strongly fluorescent in pure water, implying their potential for ion detections in aqueous media. (C) 2012 Elsevier Ltd. All rights reserved.