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Stereoselective Synthesis of 2-Deoxythiosugars from Glycals

ABSTRACT: 2-deoxythiosugars are more stable than 2-deoxysugars occurring broadly in bioactive natural products and pharmaceutical agents. An effective and direct methodology to stereoselectively synthesize α-2-deoxythioglycosides catalyzed by AgOTf has been developed. Various alkyl thiols and thiophenols were explored and the desired products were formed in good yields with excellent α-selectivity. This method was further applied to the syntheses of S-linked disaccharides and late-stage 2-deoxyglycosylation of estrogen, L-menthol, and zingerone thiols successfully.

SUBMITTER: You X

PROVIDER: S-EPMC9696349 | biostudies-literature | 2022 Nov

REPOSITORIES: biostudies-literature

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