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Issue 43, 2012
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Organosilicon-mediated regioselective acetylation of carbohydrates

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Abstract

Organosilicon-mediated, regioselective acetylation of vicinal- and 1,3-diols is presented. Methyl trimethoxysilane or dimethyl dimethoxysilane was first used to form cyclic 1,3,2-dioxasilolane or 1,3,2-dioxasilinane intermediates, and subsequent acetate-catalyzed monoacylation was efficiently performed by addition of acetic anhydride or acetyl chloride under mild conditions. The reaction exhibited high regioselectivity, resulting in the same protection pattern as in organotin-mediated schemes.

Graphical abstract: Organosilicon-mediated regioselective acetylation of carbohydrates

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Publication details

The article was received on 01 Mar 2012, accepted on 03 Apr 2012 and first published on 10 Apr 2012


Article type: Communication
DOI: 10.1039/C2CC31556D
Citation: Chem. Commun., 2012,48, 5370-5372
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    Organosilicon-mediated regioselective acetylation of carbohydrates

    Y. Zhou, O. Ramström and H. Dong, Chem. Commun., 2012, 48, 5370
    DOI: 10.1039/C2CC31556D

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