Abstract
The preparation of a δ-dicarbonyl sugar thorough ring-opening, by a methoxymercuration–demercuration procedure, of a 5-spirocyclopropanated d-galactose derivative, is reported. This method constitutes a new route for the transformation of a hexose into new and interesting δ-dicarbonyl sugars, synthetic precursors of cyclitols, carba- and azasugars. Moreover this is, to our best knowledge, the first reported example of an elongation to a higher sugar starting from a spirocyclopropanated saccharide.
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