Towards the synthesis of new dideoxy delta-dicarbonyl heptoses.
The preparation of a delta-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 delta-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.
Pistarà
Venerando
V
Università di Catania, Dipartimento di Scienze Chimiche, I-95125 Catania, Italy. vpistara@unict.it
Chiacchio
Maria Assunta
MA
Corsaro
Antonino
A
D005690:Galactose / Q000737:chemistry; D006539:Heptoses / Q000138:chemical synthesis* / Q000737:chemistry*; D057927:Hydrophobic and Hydrophilic Interactions; D010084:Oxidation-Reduction
D006539:Heptoses; D005690:Galactose