Naslov
C-Linked Glycomimetic Libraries Accessed by the Passerini Reaction

Autori
Vlahoviček-Kahlina, Kristina ; Suć Sajko, Josipa ; Jerić, Ivanka

Izvornik
International journal of molecular sciences (1422-0067) 20 (2019), 24; 6236, 19

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
multicomponent reactions ; carbohydrates ; diastereoselective synthesis ; glycosylation ; C-glycosides

Sažetak
Carbohydrates and their conjugates are the most abundant natural products, with diverse and highly important biological roles. Synthetic glycoconjugates are versatile tools used to probe biological systems and interfere with them. In an endeavor to provide an efficient route to glycomimetics comprising structurally diverse carbohydrate units, we describe herein a robust, stereoselective, multicomponent approach. Isopropylidene-protected carbohydrate- derived aldehydes and ketones were utilized in the Passerini reaction, giving different glycosylated structures in high yields and diastereoselectivities up to 90:10 diastereomeric ratio (d.r). Access to highly valuable building blocks based on α-hydroxy C- glycosyl acids or more complex systems was elaborated by simple post-condensation methodologies

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA