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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 11
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Original Articles

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

, , &
Pages 1557-1562 | Received 23 Nov 2011, Published online: 06 Mar 2013
 

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.

Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file.

GRAPHICAL ABSTRACT

ACKNOWLEDGMENTS

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

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