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Issue 70, 2018
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Efficient and regioselective synthesis of γ-lactone glycosides through a novel debenzylative cyclization reaction

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Abstract

An efficient and regioselective approach for the construction of synthetically important γ-lactone glycosides is reported from unprotected aldoses through a new debenzylative lactonization (DBL) reaction. The scope and limitations of this DBL reaction are described starting from a series of commercially available hexoses (L-fucose, D-galactose, D-glucose) and pentoses (D-arabinose, D-ribose, D-lyxose, D-xylose) to afford the corresponding γ-lactones in good yields and without concomitant δ-lactone formation.

Graphical abstract: Efficient and regioselective synthesis of γ-lactone glycosides through a novel debenzylative cyclization reaction

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Publication details

The article was received on 09 Jul 2018, accepted on 06 Aug 2018 and first published on 11 Aug 2018


Article type: Communication
DOI: 10.1039/C8CC05523H
Citation: Chem. Commun., 2018,54, 9845-9848
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    Efficient and regioselective synthesis of γ-lactone glycosides through a novel debenzylative cyclization reaction

    J. A. Delbrouck, A. Tikad and S. P. Vincent, Chem. Commun., 2018, 54, 9845
    DOI: 10.1039/C8CC05523H

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