Dondoni Alessandro, Giovannini Pier Paolo, Massi Alessandro
Laboratorio di Chimica Organica, Dipartimento di Chimica, Università di Ferrara, Via L. Borsari 46, I-44100 Ferrara, Italy.
Org Lett. 2004 Aug 19;6(17):2929-32. doi: 10.1021/ol048963g.
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.
C-糖基腈氧化物与乙炔的1,3-偶极环加成反应以及与分别带有掩蔽甘氨酰部分的炔烃和叠氮化物的反应，分别得到了二取代异恶唑和三唑。在这些环加成产物中揭示甘氨酰基团得到了C-糖基α-氨基酸，其中两个生物活性实体通过刚性五元杂环相连。合成相同化合物的优化方法涉及使用未掩蔽但受保护的含炔烃和叠氮化物的氨基酸作为1,3-偶极环加成反应的反应物。
