methyl 6-[4-(β-D-galactopyranosyl)-1H-1,2,3-triazol-1-yl]-6-deoxy-α-D-glucopyranoside | 1015236-31-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-[4-(β-D-galactopyranosyl)-1H-1,2,3-triazol-1-yl]-6-deoxy-α-D-glucopyranoside
• 英文别名: (2S,3R,4S,5S,6R)-2-methoxy-6-[[4-[(2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]triazol-1-yl]methyl]oxane-3,4,5-triol
• CAS: 1015236-31-3
• 化学式: C₁₅H₂₅N₃O₁₀
• 分子量: 407.378
• InChiKey: SCAJYRXKIATYOY-ATCGGQGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.9
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  200
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-deoxy-6-[4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-1H-1,2,3-triazol-1-yl]-α-D-glucopyranoside 在 palladium dihydroxide 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 以94%的产率得到methyl 6-[4-(β-D-galactopyranosyl)-1H-1,2,3-triazol-1-yl]-6-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Validation of the Copper(I)-Catalyzed Azide−Alkyne Coupling in Ionic Liquids. Synthesis of a Triazole-Linked C-Disaccharide as a Case Study

  摘要：

  The first study of a copper(I)-catalyzed azide-alkyne click reaction in ionic liquids (ILs) is reported. The cycloaddition of a sugar azide with a sugar acetylene (CuI, i-Pr2EtN, 80 degrees C) was carried out in 10 ILs as well as in standard molecular solvents (toluene and DMF) to give the 1,4-disubstituted triazole-linked C-disaccharide. The highest yields (84 and 95%) were registered in Ammoeng 110 and [C(8)dabco][N(CN)(2)]. The latter solvent was recycled in four subsequent reactions without loss of the reaction efficiency. Reactions carried out in the absence of the Hunig's base afforded mixtures of 1,4- and 1,5-disubstituted triazole regioisomers.

  DOI：

  10.1021/jo7026454

文献信息

• Validation of the Copper(I)-Catalyzed Azide−Alkyne Coupling in Ionic Liquids. Synthesis of a Triazole-Linked <i>C</i>-Disaccharide as a Case Study
  作者：Alberto Marra、Alessandra Vecchi、Cinzia Chiappe、Bernardo Melai、Alessandro Dondoni

  DOI：10.1021/jo7026454

  日期：2008.3.1

  The first study of a copper(I)-catalyzed azide-alkyne click reaction in ionic liquids (ILs) is reported. The cycloaddition of a sugar azide with a sugar acetylene (CuI, i-Pr2EtN, 80 degrees C) was carried out in 10 ILs as well as in standard molecular solvents (toluene and DMF) to give the 1,4-disubstituted triazole-linked C-disaccharide. The highest yields (84 and 95%) were registered in Ammoeng 110 and [C(8)dabco][N(CN)(2)]. The latter solvent was recycled in four subsequent reactions without loss of the reaction efficiency. Reactions carried out in the absence of the Hunig's base afforded mixtures of 1,4- and 1,5-disubstituted triazole regioisomers.