title: 5'-Spiro-cyclopropanated lactose derivatives as suitable intermediates for the chain elongation: synthesis of a new 6-deoxy-6-methyl δ-eptulose.
abstract: 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.
authors: Dipartimento di Scienze del Farmaco, Università di Catania, viale A. Doria 6, I-95125 Catania, Italy. Electronic address: vpistara@unict.it.
authors: Venerando
authors: V
authors: Pistarà
authors: Dipartimento di Scienze del Farmaco, Università di Catania, viale A. Doria 6, I-95125 Catania, Italy.
authors: Antonio
authors: A
authors: Rescifina
authors: Dipartimento di Scienze del Farmaco, Università di Catania, viale A. Doria 6, I-95125 Catania, Italy.
authors: Antonino
authors: A
authors: Corsaro
mesh_terms: D002236:Carbohydrate Conformation; D060326:Chemistry Techniques, Synthetic; D007785:Lactose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D013141:Spiro Compounds / Q000737:chemistry*
chemical_list: C000611894:6-deoxy-6-methyl delta-eptulose; D013141:Spiro Compounds; D007785:Lactose
keywords: Chain elongation; Cyclopropanation; In silico studies; Lactose; δ-dicarbonyl heptose