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A streamlined strategy for aglycone assembly and glycosylation.

ABSTRACT: Multipurpose sugars: Carbohydrate-derived silane reagents are utilized as the reductant for nickel-catalyzed aldehyde-alkyne reductive coupling reactions and as the glycosyl donor for subsequent intramolecular glycosylation. The approach enables the assembly of the carbon-carbon framework and stereochemical features of an aglycone while simultaneously establishing the site of glycosylation.

SUBMITTER: Partridge KM

PROVIDER: S-EPMC3867577 | biostudies-literature | 2013 Dec

REPOSITORIES: biostudies-literature

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A streamlined strategy for aglycone assembly and glycosylation.

Partridge Katherine M KM Bader Scott J SJ Buchan Zachary A ZA Taylor Christopher E CE Montgomery John J

Angewandte Chemie (International ed. in English) 20131021 51

Multipurpose sugars: Carbohydrate-derived silane reagents are utilized as the reductant for nickel-catalyzed aldehyde-alkyne reductive coupling reactions and as the glycosyl donor for subsequent intramolecular glycosylation. The approach enables the assembly of the carbon-carbon framework and stereochemical features of an aglycone while simultaneously establishing the site of glycosylation. ...[more]

PMID: 24151089

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