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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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Stereoselective Synthesis of 2-Deoxythiosugars from Glycals.

You Xueying X   Cai Yifei Y   Xiao Chenyu C   Ma Lijuan L   Wei Yong Y   Xie Tianpeng T   Chen Lei L   Yao Hui H  

Molecules (Basel, Switzerland) 20221117 22

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 <i>S</i>-linked disaccharides and late-stage 2-deoxyglyc  ...[more]

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