3,5-dideoxy-5-[4-(2',1',3'-benzothiadiazol-4'-yl)-1,2,3-triazol-1-yl]-3-(pyridin-2'-yl-1,2,3-triazol-1-yl)-1,2-O-isopropylidene-α-D-xylofuranose | 1341163-78-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3,5-dideoxy-5-[4-(2',1',3'-benzothiadiazol-4'-yl)-1,2,3-triazol-1-yl]-3-(pyridin-2'-yl-1,2,3-triazol-1-yl)-1,2-O-isopropylidene-α-D-xylofuranose
• 英文别名: 4-[1-[[(3aR,5R,6S,6aR)-2,2-dimethyl-6-(4-pyridin-2-yltriazol-1-yl)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl]triazol-4-yl]-2,1,3-benzothiadiazole
• CAS: 1341163-78-7
• 化学式: C₂₃H₂₁N₉O₃S
• 分子量: 503.544
• InChiKey: CDZQSHIGDLNOFM-FVTFTPSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  156
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3,5-dideoxy-5-[4-(2',1',3'-benzothiadiazol-4'-yl)-1,2,3-triazol-1-yl]-3-(pyridin-2'-yl-1,2,3-triazol-1-yl)-1,2-O-isopropylidene-α-D-xylofuranose 、 copper(II) perchlorate 以 二甲基亚砜 、 乙腈 为溶剂， 生成 [3,5-dideoxy-5-[4-(2',1',3'-benzothiadiazol-4'-yl)-1,2,3-triazol-1-yl]-3-(pyridin-2'-yl-1,2,3-triazol-1-yl)-1,2-O-isopropylidene-α-D-xylofuranose]Cu(2+)
  参考文献：
  名称：

  Intrinsically Fluorescent Glycoligands To Study Metal Selectivity

  摘要：

  Glycoligands are a versatile family of ligands centered on a sugar platform and functionalized by Lewis bases. In this article, pentofuranoses were appended with the fluoroionophores 4-(pyridin-2'-yl)-1,2,3-triazol-1-yl and 4-(2',1',3'-benzothiadiazol-4'-yl)-1,2,3-triazol-1-yl using the "click-like" cycloaddition [2 + 3] of Huisgen catalyzed by copper(I). Their fluorescence properties were used to study metal cation complexation. A possible selective functionalization of furanoscaffolds allows the synthesis of "mixed" glycoligands with the successive insertion of these different fluoroionophores. The metal selectivity and the chelating behavior of these six resulting intrinsically fluorescent glycoligands were investigated. The change in the configuration at the carbon C3 of furanose did not influence either the metal selectivity or the binding constants. However, different selectivities and binding constants were found to depend on the nature of the fluoroionophore moieties. Overall, the triazolylbenzothiadiazolyl chelating group was shown to be less efficient than the triazolylpyridyl claw for complexation. Interestingly enough, the triazolylbenzothiadiazolyl claw, which fluoresces in the visible range, did not interfere in the binding and selectivity of the more efficient triazolylpyridyl claw. This study suggests that the triazolylbenzothiadiazolyl moiety could be used as an adequate fluorescent reporter to qualitatively monitor complexation of other moieties.

  DOI：

  10.1021/ic200897v
• 作为产物：
  描述：

  3-deoxy-1,2-O-isopropylidene-3-(pyridin-2'-yl-1,2,3-triazol-1-yl)-α-D-xylofuranose 在 吡啶 、 sodium azide 、 四丁基氟化铵 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 5.0h， 生成 3,5-dideoxy-5-[4-(2',1',3'-benzothiadiazol-4'-yl)-1,2,3-triazol-1-yl]-3-(pyridin-2'-yl-1,2,3-triazol-1-yl)-1,2-O-isopropylidene-α-D-xylofuranose
  参考文献：
  名称：

  Intrinsically Fluorescent Glycoligands To Study Metal Selectivity

  摘要：

  Glycoligands are a versatile family of ligands centered on a sugar platform and functionalized by Lewis bases. In this article, pentofuranoses were appended with the fluoroionophores 4-(pyridin-2'-yl)-1,2,3-triazol-1-yl and 4-(2',1',3'-benzothiadiazol-4'-yl)-1,2,3-triazol-1-yl using the "click-like" cycloaddition [2 + 3] of Huisgen catalyzed by copper(I). Their fluorescence properties were used to study metal cation complexation. A possible selective functionalization of furanoscaffolds allows the synthesis of "mixed" glycoligands with the successive insertion of these different fluoroionophores. The metal selectivity and the chelating behavior of these six resulting intrinsically fluorescent glycoligands were investigated. The change in the configuration at the carbon C3 of furanose did not influence either the metal selectivity or the binding constants. However, different selectivities and binding constants were found to depend on the nature of the fluoroionophore moieties. Overall, the triazolylbenzothiadiazolyl chelating group was shown to be less efficient than the triazolylpyridyl claw for complexation. Interestingly enough, the triazolylbenzothiadiazolyl claw, which fluoresces in the visible range, did not interfere in the binding and selectivity of the more efficient triazolylpyridyl claw. This study suggests that the triazolylbenzothiadiazolyl moiety could be used as an adequate fluorescent reporter to qualitatively monitor complexation of other moieties.

  DOI：

  10.1021/ic200897v

文献信息

• Intrinsically Fluorescent Glycoligands To Study Metal Selectivity
  作者：Ludivine Garcia、Stéphane Maisonneuve、Jennifer Oudinet-Sin Marcu、Régis Guillot、François Lambert、Juan Xie、Clotilde Policar

  DOI：10.1021/ic200897v

  日期：2011.11.21

  Glycoligands are a versatile family of ligands centered on a sugar platform and functionalized by Lewis bases. In this article, pentofuranoses were appended with the fluoroionophores 4-(pyridin-2'-yl)-1,2,3-triazol-1-yl and 4-(2',1',3'-benzothiadiazol-4'-yl)-1,2,3-triazol-1-yl using the "click-like" cycloaddition [2 + 3] of Huisgen catalyzed by copper(I). Their fluorescence properties were used to study metal cation complexation. A possible selective functionalization of furanoscaffolds allows the synthesis of "mixed" glycoligands with the successive insertion of these different fluoroionophores. The metal selectivity and the chelating behavior of these six resulting intrinsically fluorescent glycoligands were investigated. The change in the configuration at the carbon C3 of furanose did not influence either the metal selectivity or the binding constants. However, different selectivities and binding constants were found to depend on the nature of the fluoroionophore moieties. Overall, the triazolylbenzothiadiazolyl chelating group was shown to be less efficient than the triazolylpyridyl claw for complexation. Interestingly enough, the triazolylbenzothiadiazolyl claw, which fluoresces in the visible range, did not interfere in the binding and selectivity of the more efficient triazolylpyridyl claw. This study suggests that the triazolylbenzothiadiazolyl moiety could be used as an adequate fluorescent reporter to qualitatively monitor complexation of other moieties.