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

Dedicated to Prof. Armin de Meijere on the occasion of his 80^th birthday

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 Introduction

2 C-Glycosylation of Benzylated Glycosyl Donors

3 C-Glycosylation of Silylated Glycosyl Donors

4 Conclusion

Key words

carbohydrates - C-glycosylation - umpolung - Corey–Seebach reaction - natural products - scleropentasides

• References and Notes

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