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TMSBr-mediated solvent- and work-up-free synthesis of ?-2-deoxyglycosides from glycals.

ABSTRACT: The thio-additions of glycals were efficiently promoted by a stoichiometric amount of trimethylsilyl bromide (TMSBr) to produce S-2-deoxyglycosides under solvent-free conditions in good to excellent yields. In addition, with triphenylphosphine oxide as an additive, the TMSBr-mediated direct glycosylations of glycals with a large range of alcohols were highly ?-selective.

SUBMITTER: Hsu MY

PROVIDER: S-EPMC4979735 | biostudies-literature | 2016

REPOSITORIES: biostudies-literature

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TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals.

Hsu Mei-Yuan MY Liu Yi-Pei YP Lam Sarah S Lin Su-Ching SC Wang Cheng-Chung CC

Beilstein journal of organic chemistry 20160804

The thio-additions of glycals were efficiently promoted by a stoichiometric amount of trimethylsilyl bromide (TMSBr) to produce S-2-deoxyglycosides under solvent-free conditions in good to excellent yields. In addition, with triphenylphosphine oxide as an additive, the TMSBr-mediated direct glycosylations of glycals with a large range of alcohols were highly α-selective. ...[more]

PMID: 27559420

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