2-nitro thioglycoside donors: versatile precursors of beta-D-glycosides of aminosugars.
2-Nitro thioglycosides can be prepared by the Michael addition of thiophenol to 2-nitroglycal derivatives. NIS/TMSOTf activation of these 2-nitro thioglycosides, in the presence of alcohols, rapidly and cleanly led to the desired glycosides in good yield and beta-selectivity. Reduction of the nitro group allowed generation of the corresponding 2-acetamido glycosides.
Barroca
Nadine
N
Department of Chemistry, University of Konstanz, Fach M 725, 78457 Konstanz, Germany.
Schmidt
Richard R
RR
D000606:Amino Sugars / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis*; D013865:Thioglycosides / Q000737:chemistry*
D000606:Amino Sugars; D006027:Glycosides; D013865:Thioglycosides