Assembling Heterocycle-Tethered C -Glycosyl and α-Amino Acid Residues via 1,3-Dipolar Cycloaddition Reactions
2004; American Chemical Society; Volume: 6; Issue: 17 Linguagem: Inglês
10.1021/ol048963g
ISSN1523-7060
AutoresAlessandro Dondoni, Pier Paolo Giovannini, Alessandro Massi,
Tópico(s)Chemical Synthesis and Analysis
ResumoThe 1,3-dipolar cycloadditions of C-glycosyl nitrile oxides and acetylenes to an alkyne and an azide, respectively, bearing a masked glycinyl moiety furnished disubstituted isoxazoles and triazoles. Unveiling the glycinyl group in these cycloadducts afforded C-glycosyl α-amino acids in which the two bioactive entities were tethered through rigid five-membered heterocycles. Optimized entries to the same compounds involved the use of unmasked but protected alkyne- and azide-containing amino acids as the partners of 1,3-dipolar cycloadditions.
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