Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
5 years ago

3-Aminodeoxypyranoses in Glycosylation: Diversity-Oriented Synthesis and Assembly in Oligosaccharides

3-Aminodeoxypyranoses in Glycosylation: Diversity-Oriented Synthesis and Assembly in Oligosaccharides
Guangfei Sun, Jing Zeng, Qian Wan, Ruobin Wang, Wang Yao, Xue-Wei Liu, Yangbin Zhu, Lei Cai, Qian Zhang, Ke Liu
A concise, diversity-oriented approach for the synthesis of naturally occurring 3-amino- and 3-nitro-2,3,6-trideoxypyranose derivatives and analogues thereof from simple sugars has been developed. In addition, we investigated the synthesis of various 3-aminoglycosyl donors and their application in glycosylation reactions. These studies led to the successful synthesis of a tetrasaccharide containing four different 3-aminosugar components using ortho-alkynylbenzoate donors. A diversity-oriented approach for the synthesis of naturally occurring 3-amino- and 3-nitro-2,3,6-trideoxypyranose derivatives from simple sugars has been developed. These studies led to the successful synthesis of a tetrasaccharide containing four different 3-aminosugar components by stereoselective glycosylation of ortho-alkynylbenzoate donors.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201700178

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