Synthesis of a Dual-Purpose 2-Deoxy-2-fluoro-glucopyranosyl Building Block

Abstract

We demonstrate a straightforward route to 1,3,6-tri-O-acetyl-4-O-benzyl-2-deoxy-2-fluoro-D-glucopyranose through potassium hydrogen fluoride opening of a Černý epoxide under microwave irradiation followed by acetolysis. The fluoroglucose building block was used as a key intermediate in the synthesis of 2,2′-dideoxy-2,2′-difluoromaltose.

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GRAPHICAL ABSTRACT

Keywords:

• Epoxide opening
• glycosylation
• maltose
• microwave

ACKNOWLEDGMENTS

We are grateful for support from the Carlsberg Foundation and the OChem Graduate School, Aarhus University.