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Versatile Glycosyl Sulfonates in ?-Selective C-Glycosylation.

ABSTRACT: C-Glycosides are both a common motif in many bioactive natural products and important glycoside mimetics. We demonstrate that activating a hemiacetal with a sulfonyl chloride, followed by treating the resultant glycosyl sulfonate with an enolate results in the stereospecific construction of ?-linked C-glycosides. This reaction tolerates a range of acceptors and donors, including disaccharides. The resulting products can be readily derivatized into C-glycoside analogues of ?-glycoconjugates, including C-disaccharide mimetics.

SUBMITTER: Ling J

PROVIDER: S-EPMC7054165 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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Versatile Glycosyl Sulfonates in β-Selective C-Glycosylation.

Ling Jesse J Bennett Clay S CS

Angewandte Chemie (International ed. in English) 20200203 11

C-Glycosides are both a common motif in many bioactive natural products and important glycoside mimetics. We demonstrate that activating a hemiacetal with a sulfonyl chloride, followed by treating the resultant glycosyl sulfonate with an enolate results in the stereospecific construction of β-linked C-glycosides. This reaction tolerates a range of acceptors and donors, including disaccharides. The resulting products can be readily derivatized into C-glycoside analogues of β-glycoconjugates, incl ...[more]

PMID: 31880395

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