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Synlett 2019; 30(17): 1935-1939
DOI: 10.1055/s-0039-1690158
DOI: 10.1055/s-0039-1690158
synpacts
β-Selective One-Pot Synthesis of Acyl-C-Glycosides via Corey–Seebach Umpolung Reaction
Generous financial support of this research by the Fonds der Chemischen Industrie is gratefully acknowledged. G.J.B. thanks the Universität Hamburg for a PhD fellowship (Hamburg Stipendium).Further Information
Publication History
Received: 05 July 2019
Accepted after revision: 25 July 2019
Publication Date:
13 August 2019 (online)
Dedicated to Prof. Armin de Meijere on the occasion of his 80th 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
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