Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 12, Pages 5245-5254Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo300791v
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Funding
- Nanyang Technological University [RG50/08]
- Ministry of Education, Singapore [MOE 2009-T2-1-030]
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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 alpha-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.
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