Triazole-fused sugars from nitroalkene-containing C-glycosides by a tandem 1,3-dipolar cycloaddition and intramolecular Michael addition |
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| Authors: | Wei Zou Milan Bhasin Kannan Vembaiyan Dean T Williams |
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| Affiliation: | Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario, Canada K1A 0R6 |
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| Abstract: | A synthetic method to triazole-fused sugars by treatment of nitroalkene-containing C-glycosides with sodium azide is described. Initial experiments conducted at room temperature gave only the 1,3-dipolar cycloaddition products. However, at elevated reaction temperature the tandem β-elimination/cycloaddition/Michael addition yielded 1,5-disubstituted triazole-fused sugars. |
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| Keywords: | Synthesis Triazole C-Glycoside Nitroalkene Cycloaddition Michael addition |
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