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Issue 40, 2013
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An approach to 8 stereoisomers of homonojirimycin from d-glucosevia kinetic & thermodynamic azido-γ-lactones

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Abstract

Crystal structures were obtained for the two C2 epimeric azido-γ-lactones 2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-D-glycero-D-ido-heptono-1,4-lactone and 2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-D-glycero-D-gulo-heptono-1,4-lactone prepared from kinetic and thermodynamic azide displacements of a triflate derived from D-glucoheptonolactone. Azido-γ-lactones are very useful intermediates in the synthesis of iminosugars and polyhydroxylated amino acids. In this study two epimeric azido-heptitols allow biotechnological transformations via Izumoring techniques to 8 of the 16 possible homonojirimycin analogues, 5 of which were isolated pure because of the lack of stereoselectivity of the final reductive amination. A side-by-side glycosidase inhibition profile of 11 of the possible 16 HNJ stereoisomers derived from D-glucose and D-mannose is presented.

Graphical abstract: An approach to 8 stereoisomers of homonojirimycin from d-glucose via kinetic & thermodynamic azido-γ-lactones

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Article information


Submitted
28 Jun 2013
Accepted
12 Aug 2013
First published
14 Aug 2013

Org. Biomol. Chem., 2013,11, 6886-6899
Article type
Paper

An approach to 8 stereoisomers of homonojirimycin from D-glucose via kinetic & thermodynamic azido-γ-lactones

A. F. G. Glawar, S. F. Jenkinson, S. J. Newberry, A. L. Thompson, S. Nakagawa, A. Yoshihara, K. Akimitsu, K. Izumori, T. D. Butters, A. Kato and G. W. J. Fleet, Org. Biomol. Chem., 2013, 11, 6886
DOI: 10.1039/C3OB41334A

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