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Issue 39, 2013
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Nickel-catalyzed α-glycosylation of C(1)-hydroxyl D-myo-inositol: a formal synthesis of mycothiol

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Abstract

Formal synthesis of mycothiol has been developed via nickel-catalyzed α-glycosylation of the C(1)-hydroxyl group of D-myo-inositols with C(2)-N-substituted benzylideneamino N-phenyl trifluoroacetimidate donors. The pseudo-oligosaccharides were obtained in good yield and with excellent α-selectivity. Removal of the C(2)-N-2-trifluoromethylphenyl-benzylidene group under mild conditions provides a pseudo-disaccharide, completing the formal synthesis of mycothiol.

Graphical abstract: Nickel-catalyzed α-glycosylation of C(1)-hydroxyl d-myo-inositol: a formal synthesis of mycothiol

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Publication details

The article was received on 11 Aug 2012, accepted on 31 Aug 2012 and first published on 03 Sep 2012


Article type: Communication
DOI: 10.1039/C2CC35823A
Citation: Chem. Commun., 2013,49, 4313-4315
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    Nickel-catalyzed α-glycosylation of C(1)-hydroxyl D-myo-inositol: a formal synthesis of mycothiol

    M. S. McConnell, F. Yu and H. M. Nguyen, Chem. Commun., 2013, 49, 4313
    DOI: 10.1039/C2CC35823A

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