Assembling heterocycle-tethered C-glycosyl and alpha-amino acid residues via 1,3-dipolar cycloaddition reactions |
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Authors: | Dondoni Alessandro Giovannini Pier Paolo Massi Alessandro |
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Institution: | Laboratorio di Chimica Organica, Dipartimento di Chimica, Università di Ferrara, Via L. Borsari 46, I-44100 Ferrara, Italy. adn@dns.unife.it |
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Abstract: | The 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 alpha-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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