Synthesis of C2-symmetric Glycophanes Through a 'Click Chemistry' Approach

被引：3

作者：

Balou, Gildas R. ^{[1
]}

Joly, Jean-Pierre ^{[1
]}

Vernex-Loset, Lionel ^{[2
]}

Chapleur, Yves ^{[1
]}

机构：

[1] Nancy Univ, Grp Sucres, UMR 7565, CNRS, F-54506 Vandoeuvre Les Nancy, France

[2] Univ Paul Verlaine, Lab Spectrometrie Masse & Chim Laser, F-57078 Metz 3, France

来源：

LETTERS IN ORGANIC CHEMISTRY | 2009年 / 6卷 / 02期

关键词：

carbohydrate; Ferrier reaction; Huisgen cycloaddition; click chemistry; glycophane; WATER-SOLUBLE CYCLOPHANES; PAUSON-KHAND REACTION; 1,3-DIPOLAR CYCLOADDITION; CYCLODEXTRIN ANALOGS; TERMINAL ALKYNES; MACROCYCLES; ROUTE; RECEPTORS; AZIDES; MODEL;

D O I：

10.2174/157017809787582843

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of C-2-symmetric glycophanes incorporating two triazole linkers has been achieved in seven steps from 3,4,6-tri-O-acetyl-D-glucal in good overall yields. The intermolecular Cu( I)-mediated Huisgen reaction was used for the ring closure key-step to give almost exclusively 24-, 26-, and 32-membered chiral macrocycles without significant polymerization. Target compounds however had low solubility in water, precluding investigation of their recognition behaviour in this medium.

引用

页码：106 / 109

页数：4

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