A δ-dicarbonyl heptose has been prepared through an electrophilic ring opening procedure of a 5'-spirocyclopropanated lactose derivative. The reported synthetic procedure outlines a new route for the transformation of this renewable disaccharide into new and interesting δ-dicarbonyl sugars, synthetic precursors of cyclitols, carba- and azasugars. The experimental results of the cyclopropanation process have been successfully rationalized by in silico studies.
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