Synthesis of 2-Deoxyglycosides with Exclusive β-Configuration Using 2-SAc Glycosyl Bromide Donors
Yang-Fan Guo1, Tian-Tian Xu1, Guo-Hui Zhang1
1Key Laboratory of Material Chemistry for Energy Conversion and Storage, Hubei Key Laboratory of Bioinorganic Chemistry and Materia Medica, School of Chemistry & Chemical Engineering, Huazhong University of Science & Technology, Ministry of Education, Luoyu Road 1037, Wuhan 430074, China.
Abstract:
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-CH3COOH 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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