Details

Autor(en) / Beteiligte

• Wu, Jun
• Kopp, Adelina
• Ackermann, Lutz

Titel

Synthesis of C‐Oligosaccharides through Versatile C(sp3)−H Glycosylation of Glycosides

Ist Teil von

• Angewandte Chemie (International ed.), 2022-03, Vol.61 (11), p.e202114993-n/a

Auflage

International ed. in English

Ort / Verlag

Germany: Wiley Subscription Services, Inc

Erscheinungsjahr

2022

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• C‐oligosaccharides are pharmacologically relevant because they are more hydrolysis‐resistant than O‐oligosaccharides. Despite indisputable advances, C‐oligosaccharides continue to be underdeveloped, likely due to a lack of efficient and selective strategies for the assembly of the interglycosidic C−C linkages. In contrast, we, herein, report a versatile and robust strategy for the synthesis of structurally complex C‐oligosaccharides via catalyzed C(sp3)−H activations. Thus, a wealth of complex interglycosidic (2→1)‐ and (1→1)‐C‐oligosaccharides becomes readily available by palladium‐catalyzed C(sp3)−H glycoside glycosylation. The isolation of key palladacycle intermediates and experiments with isotopically‐labeled compounds identified a trans‐stereoselectivity for the C(sp3)−H glycosylation. The glycoside C(sp3)−H activation manifold was likewise exploited for the diversification of furanoses, pyranoses and disaccharides. The palladium‐catalyzed C(sp3)−H glycosylation of glycosides is disclosed. This saccharide assembly by C(sp3)−H glycosylation featured excellent site‐ and stereoselectivity and enabled the efficient synthesis of diverse C‐disaccharides and C‐trisaccharides.