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Stereoselective Glycosylation of 2-Nitrogalactals Catalyzed by a Bifunctional Organocatalyst.

ABSTRACT: The use of a bifunctional cinchona/thiourea organocatalyst for the direct and α-stereoselective glycosylation of 2-nitrogalactals is demonstrated for the first time. The conditions are mild, practical, and applicable to a wide range of glycoside acceptors with products being isolated in good to excellent yields. The method is exemplified in the synthesis of mucin type Core 6 and 7 glycopeptides.

SUBMITTER: Medina S

PROVIDER: S-EPMC5049936 | biostudies-literature | 2016 Sep

REPOSITORIES: biostudies-literature

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Stereoselective Glycosylation of 2-Nitrogalactals Catalyzed by a Bifunctional Organocatalyst.

Medina Sandra S Harper Matthew J MJ Balmond Edward I EI Miranda Silvia S Crisenza Giacomo E M GE Coe Diane M DM McGarrigle Eoghan M EM Galan M Carmen MC

Organic letters 20160816 17

The use of a bifunctional cinchona/thiourea organocatalyst for the direct and α-stereoselective glycosylation of 2-nitrogalactals is demonstrated for the first time. The conditions are mild, practical, and applicable to a wide range of glycoside acceptors with products being isolated in good to excellent yields. The method is exemplified in the synthesis of mucin type Core 6 and 7 glycopeptides. ...[more]

PMID: 27529800

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