期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 80, 期 21, 页码 10719-10733出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01938
关键词
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资金
- CNRS
- University of Strasbourg
- Centre International de Recherche aux Frontieres de la Chimie (FRC)
- Institut Universitaire de France (IUF)
- French Ministry of Research
A modular strategy has been developed to access a diversity of cyclic and acyclic oligosaccharide analogues designed as prefunctionalized scaffolds for the synthesis of multivalent ligands. This convergent approach is based on bifunctional sugar building blocks with two temporarily masked functionalities that can be orthogonally activated to perform Cu(I)-catalyzed azide-alkyne cycloaddition reactions (CuAAC). The reducing end is activated as a glycosyl azide and masked as a 1,6-anhydro sugar, while the nonreducing end is activated as a free alkyne and masked as a triethylsilyl-alkyne. Following a cyclooligomerization approach, the first examples of close analogues of cyclodextrins composed of D-glucose residues and triazole units bound together through alpha-(1,4) linkages were obtained. The cycloglucopyranoside analogue containing four sugar units was used as a template to prepare multivalent systems displaying a protected D-mannose derivative or an iminosugar by way of CuAAC. On the other hand, the modular approach led to acyclic alkyne-functionalized scaffolds of a controlled size that were used to synthesize multivalent iminosugars.
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