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 | 1015236-27-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• 英文别名: 1-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl]-4-[(2S,3S,4R,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]triazole
• CAS: 1015236-27-7
• 化学式: C₆₄H₆₇N₃O₁₀
• 分子量: 1038.25
• InChiKey: QOBWEEBUELVONO-YEOVSIOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  77
• 可旋转键数：
  26
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (2R,3R,4S,5R,6S)-2-Azidomethyl-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran 、 3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-mannooctitol 在 copper(l) iodide 作用下， 以68%的产率得到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
  参考文献：
  名称：

  无胺条件下离子液体中铜（I）催化的叠氮化物-炔烃环加成反应

  摘要：

  在不添加游离胺的情况下，在市售的多氧化离子液体（AMMOENG 100™）中进行结构多样的有机叠氮化物和末端炔烃的各种组合的碘化亚铜（I）催化的环加成反应。与先前测试过的离子液体不同，该溶剂仅产生1,4-二取代的三唑区域异构体。 炔烃-叠氮化物-碳水化合物-铜-环加成

  DOI：

  10.1055/s-0029-1218760

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.
• Copper(I)-Catalyzed Azide-Alkyne Cycloadditions in Ionic Liquids under Amine-Free Conditions
  作者：Alberto Marra、Alessandro Dondoni、Alessandra Vecchi、Angela Chambery、Cinzia Chiappe

  DOI：10.1055/s-0029-1218760

  日期：2010.6

  Copper(I) iodide catalyzed cycloadditions of various combinations of structurally diverse organic azides and terminal alkynes were carried out in a commercially available, polyoxygenated ionic liquid (AMMOENG 100™) without addition of free amine. Unlike the previously tested ionic liquids, this solvent led exclusively to the 1,4-disubstituted triazole regioisomer. alkynes - azides - carbohydrates -

  在不添加游离胺的情况下，在市售的多氧化离子液体（AMMOENG 100™）中进行结构多样的有机叠氮化物和末端炔烃的各种组合的碘化亚铜（I）催化的环加成反应。与先前测试过的离子液体不同，该溶剂仅产生1,4-二取代的三唑区域异构体。 炔烃-叠氮化物-碳水化合物-铜-环加成