Synlett 2019; 30(17): 1935-1939
DOI: 10.1055/s-0039-1690158
synpacts
© Georg Thieme Verlag Stuttgart · New York

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

G. Jacob Boehlich
,
Universität Hamburg, Institut für Pharmazie, Bundesstraße 45, 20146 Hamburg, Germany   Email: Nina.Schuetzenmeister@chemie.uni-hamburg.de
› Author Affiliations
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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