Triazole-fused sugars from nitroalkene-containing C-glycosides by a tandem 1,3-dipolar cycloaddition and intramolecular Michael addition

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DOIResolve DOI: http://doi.org/10.1016/j.carres.2009.03.007
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TypeArticle
Journal titleCarbohydrate Research
Volume344
Issue8
Pages10241027; # of pages: 4
SubjectSynthesis; Triazole; C-Gycoside; Nitroalkene; Cycloaddition; Michael addition
AbstractA 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.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada (NRC-CNRC); NRC Institute for Biological Sciences
Peer reviewedYes
NPARC number15329247
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Record identifierc2a7147c-01b2-4534-b999-4064604c7a85
Record created2010-05-21
Record modified2016-05-09
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