Assembling Heterocycle-Tethered C-Glycosyl and α-Amino Acid Residues via 1,3-Dipolar Cycloaddition Reactions
- 30 July 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 6 (17) , 2929-2932
- https://doi.org/10.1021/ol048963g
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 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.Keywords
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