In this study, we developed an indirect method for the synthesis of 2-deoxyglycosides with an exclusive β-configuration using glucosyl and galactosyl bromide donors with 2-thioacetyl (SAc) groups. The 2-SAc glucosyl and galactosyl bromide donors were easily obtained through the treatment of 1-OAc, 2-SAc glucose and galactose with HBr-CHCOOH solution, respectively. The glycosylation of such donors with acceptors under an improved Koenigs-Knorr condition resulted in glycosylation products with an exclusive β-configuration in excellent yields. The synthetic approach of 2-SAc glycosyl donors using glycals as the starting materials was also investigated. Based on these studies, the synthetic method of using 2-deoxyglycosides with an exclusive β-configuration through desulfurization will have more practical applications.
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