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D-Glucose was converted into a dieno-oxime and independently into a triene. Both derivatives were completely unreactive and did not undergo any cyclization: either [1,3]-dipolar cycloaddition (oxime) or [4+2] cycloaddition (triene). This result was very surprising comparing to similar examples observed by us for derivatives of ‘shorter’ sugar: D-xylose. The big difference in reactivity of the pentose and hexose derivatives is clarified by an in silico study.

Striking difference in reactivity of trienes and oximes derived from glucose and xylose