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Protecting-group-free S-glycosylation towards thioglycosides and thioglycopeptides in water.

ABSTRACT: A facile and green S-glycosylation method has been developed featuring protecting-group-free and proceeding-in-water like enzymatic synthesis. Glycosylation of fluoride donors with thiol sugar acceptors using Ca(OH)₂ as a promoter afforded various thioglycosides in good yields with exclusive stereoselectivity. This method also enabled the successful production of S-linked oligosaccharides and S-linked glycopeptides.

SUBMITTER: Zhang GL

PROVIDER: S-EPMC8423405 | biostudies-literature | 2021 Apr

REPOSITORIES: biostudies-literature

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Protecting-group-free S-glycosylation towards thioglycosides and thioglycopeptides in water.

Zhang Gao-Lan GL Gadi Madhusudhan Reddy MR Cui Xikai X Liu Ding D Zhang Jiabin J Saikam Varma V Gibbons Christopher C Wang Peng G PG Li Lei L

Green chemistry : an international journal and green chemistry resource : GC 20210301 8

A facile and green S-glycosylation method has been developed featuring protecting-group-free and proceeding-in-water like enzymatic synthesis. Glycosylation of fluoride donors with thiol sugar acceptors using Ca(OH)2 as a promoter afforded various thioglycosides in good yields with exclusive stereoselectivity. This method also enabled the successful production of S-linked oligosaccharides and S-linked glycopeptides. ...[more]

PMID: 34497476

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