Synthesis of and NMR studies on the four diastereomeric 1-deoxy-D-ketohexoses

The four 1-deoxy-d-ketohexoses-1-deoxy-d-psicose, 1-deoxy-d-fructose, 1-deoxy-d-sorbose and 1-deoxy-d-tagatose-were synthesised by methyl lithium addition to suitably protected and readily available pentonolactones. The 1-deoxy-l-ketohexoses are available from the enantiomeric lactones. The NMR stud...

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Bibliographic Details
Main Authors: Jones, N, Jenkinson, S, Soengas, R, Fanefjord, M, Wormald, M, Dwek, R, Kiran, G, Devendar, R, Takata, G, Morimoto, K, Izumori, K, Fleet, G
Format: Journal article
Language:English
Published: 2007
Description
Summary:The four 1-deoxy-d-ketohexoses-1-deoxy-d-psicose, 1-deoxy-d-fructose, 1-deoxy-d-sorbose and 1-deoxy-d-tagatose-were synthesised by methyl lithium addition to suitably protected and readily available pentonolactones. The 1-deoxy-l-ketohexoses are available from the enantiomeric lactones. The NMR studies on aqueous solutions of each diastereomer show that the relative amounts of open chain ketones, α- and β-pyranoses, and α- and β-furanoses vary considerably; at least four different species are identifiable from each equilibrium. © 2007 Elsevier Ltd. All rights reserved.