Direct and Stereoselective Synthesis of 1,3-cis-3- Arylsulphonaminodeoxydisaccharides and Oligosaccharides

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• 作者：Feiqing Ding ; Ronny William ; Shuting Cai ; Jimei Ma ; Xue-Wei Liu
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：June 15, 2012
• 年：2012
• 卷：77
• 期：12
• 页码：5245-5254
• 全文大小：438K
• 年卷期：v.77,no.12(June 15, 2012)
• ISSN：1520-6904

文摘

The 3-aminoglycosides are ubiquitous in biologically important classes of glycoconjugates and naturally occurring oligosaccharides. Despite the rapid growth in the development of synthetic method of 3-amino glycosides, the current state-of-the art suffers from limited substrate scope, low yields, long reaction times, and anomeric mixtures. This work presents a novel direct method for the synthesis of 1,3-cis-3-arylsulphonaminodeoxydisaccharides and oligosaccharides via 伪-selective glycosylation and hydroamination of glycal in a one-pot manner. This efficient multicomponent reaction methodology provides ready access to 1,3-cis-3-arylsulphonaminodeoxydisaccharides and oligosaccharides and allows derivatization by variation of each component.