Cyclohexane-1,2,3,4,5/0-pentol

No hypotheses can be advanced for the sequences involved in the oxidation of cyclohexanepentols which react even more slowly with periodate than does (+)-quercitol. For instance, when the all-trans l 3, 5/2, 4-cyclohexanepentol (33) is oxidized (Figure 6), production of malonaldehyde starts very early and the time curve of periodate reduction indicates a very complex reaction. Nor is it possible to analyze satisfactorily the curves obtained with (1 l)-1, 2, 4/3, 5-cyclohexane-pentol (34) or with dl-1, 2, 3, 4/5-cyclohexanepentol (35) [this is the configuration predicted for the (1 D)-entantiomorph (41)]. 

T. K. M. Shing and L. H. Wan, Facile synthesis of valiolamine and its diastereomers from (-)-quinic acid. Nucleophilic substitution reactions of 5-hydroxymethyl-cyclohexane-l,2,3,4,5-pentol, J. Org. Chem., 61 (1996) 8468-8479. 

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