TMSBr-mediated solvent- and work-up-free synthesis of α-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 α-selective.

Keywords

• 2-deoxyglycosides
• glycals
• trimethylsilyl bromide (TMSBr)
• triphenylphosphine oxide (TPPO)