Glycosyl thioimidates in a highly convergent one-pot strategy for oligosaccharide synthesis |
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| Institution: | 1. Department of Chemistry and Center for Therapeutics and Diagnostics, Georgia State University, Atlanta, GA 30303, USA;2. Tianjin Key Laboratory on Technologies Enabling Development of Clinical Therapeutics and Diagnostics (Theranostics), School of Pharmacy, Tianjin Medical University, Tianjin 300070, China;1. School of Molecular Bioscience, The University of Sydney, Sydney, NSW 2006, Australia;2. Department of Chemical Sciences, Complesso Universitario Monte Sant''Angelo, Napoli, Italy;1. Department of Chemistry, Faculty of Science, University of Zanjan, 45371-38791 Zanjan, Iran;2. Faculty of Chemistry, University of Wroclaw, F. Joliot-Curie 14, Wroclaw 50-383, Poland;1. Guangdong Key Laboratory of Plant Resources, School of Life Sciences, Sun Yat-sen University, Guangdong, PR China;2. Guangdong Key Laboratory of Animal Conservation and Resource Utilization, Guangdong Public Laboratory of Wild Animal Conservation and Utilization, Drug Synthesis and Evaluation Center, Guangdong Institute of Applied Biological Resources, PR China;3. Department of Chemistry, Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, PR China;1. Department of Oral Biology, School of Dental Medicine, University at Buffalo, SUNY, Buffalo, NY 14214, USA;2. Division of Chemical Biology and Medicinal Chemistry, Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, NC 27599, USA |
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| Abstract: | Application of two classes of thioimidoyl derivatives, S-benzoxazolyl (SBox) and S-thiazolyl (STaz) glycosides to selective activation over thioglycosides is described. These results allowed us to synthesize a tetrasaccharide derivative using a leaving group differentiated one-pot strategy in 73% yield over three sequential glycosylation steps. |
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