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

NA Jones, SF Jenkinson, R Soengas, M Fanefjord…

Index: Jones, Nigel A.; Jenkinson, Sarah F.; Soengas, Raquel; Fanefjord, Mette; Wormald, Mark R.; Dwek, Raymond A.; Kiran, Gullapalli P.; Devendar, Rao; Takata, Goro; Morimoto, Kenji; Izumori, Ken; Fleet, George W.J. Tetrahedron Asymmetry, 2007 , vol. 18, # 6 p. 774 - 786

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Citation Number: 34

Abstract

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, ...

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