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Benzyne-Promoted, 1,2-cis-Selective O-Glycosylation with Benzylchalcogenoglycoside Donors.

ABSTRACT: Here, we show that the reaction of benzylchalcogenoglycosides with benzyne in the presence of alcohols results in highly 1,2-cis-selective O-glycosylation in a solvent-dependent manner. Thioglycosides, selenoglycosides, and alcohols with a range of nucleophilicities lead to a productive reaction, and unusual protecting groups, auxiliary groups, and additives are avoided.

SUBMITTER: Duong T

PROVIDER: S-EPMC10696609 | biostudies-literature | 2023 Dec

REPOSITORIES: biostudies-literature

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Benzyne-Promoted, 1,2-cis-Selective O-Glycosylation with Benzylchalcogenoglycoside Donors.

Duong Tiffany T Valenzuela Erik Alvarez EA Ragains Justin R JR

Organic letters 20231116 47

Here, we show that the reaction of benzylchalcogenoglycosides with benzyne in the presence of alcohols results in highly 1,2-cis-selective O-glycosylation in a solvent-dependent manner. Thioglycosides, selenoglycosides, and alcohols with a range of nucleophilicities lead to a productive reaction, and unusual protecting groups, auxiliary groups, and additives are avoided. ...[more]

PMID: 37970840

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