Issue 39, 2013
From the journal:

Chemical Communications

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

Matthew S. McConnell,§a   Fei Yu§a  and  Hien M. Nguyen*a  

* Corresponding authors

a Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, USA
E-mail: hien-nguyen@uiowa.edu

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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Article information

DOI
https://doi.org/10.1039/C2CC35823A
Article type
Communication
Submitted
11 Aug 2012
Accepted
31 Aug 2012
First published
03 Sep 2012

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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