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Synthesis of C-Oligosaccharides through Versatile C(sp³ )-H Glycosylation of Glycosides.

ABSTRACT: 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.

SUBMITTER: Wu J

PROVIDER: S-EPMC9306939 | biostudies-literature | 2022 Mar

REPOSITORIES: biostudies-literature

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Synthesis of C-Oligosaccharides through Versatile C(sp3 )-H Glycosylation of Glycosides.

Wu Jun J Kopp Adelina A Ackermann Lutz L

Angewandte Chemie (International ed. in English) 20220127 11

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 ...[more]

PMID: 35015329

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