Triazole-fused sugars from nitroalkene-containing C-glycosides by a tandem 1,3-dipolar cycloaddition and intramolecular Michael addition.
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 beta-elimination/cycloaddition/Michael addition yielded 1,5-disubstituted triazole-fused sugars.
Zou
Wei
W
Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario, Canada. wei.zou@nrc-cnrc.gc.ca
Bhasin
Milan
M
Vembaiyan
Kannan
K
Williams
Dean T
DT
D003500:Cyclization; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D014230:Triazoles / Q000737:chemistry*
D006027:Glycosides; D014230:Triazoles