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β-Selective One-Pot Synthesis of Acyl-C-Glycosides via Corey–Seebach Umpolung Reaction

C-Glycosides are commonly used as carbohydrate mimics in drug development due to their stability against enzymatic and chemical hydrolysis. In this Synpacts article we elaborate on our fast and efficient… Click to show full abstract

C-Glycosides are commonly used as carbohydrate mimics in drug development due to their stability against enzymatic and chemical hydrolysis. In this Synpacts article we elaborate on our fast and efficient β-selective approach towards protected and unprotected acyl glycosides. Application of a Corey–Seebach umpolung reaction enables the exclusive formation of the β-anomer of aromatic acyl-C-glycosides in good to excellent yields.1 Introduction2 C-Glycosylation of Benzylated Glycosyl Donors3 C-Glycosylation of Silylated Glycosyl Donors4 Conclusion

Keywords: umpolung reaction; corey seebach; acyl; acyl glycosides; seebach umpolung

Journal Title: Synlett
Year Published: 2019

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