title: Anomeric spirocycles by solvent incorporation: reactions of O-peracylated (glyculopyranose and glyculopyranosyl bromide)onamide derivatives with ketones.
abstract: Reactions of O-peracetylated (α-D-galacto-heptulopyranosyl bromide)onamide and O-perbenzoylated (α-D-gluco-heptulopyranosyl bromide)onamide with ketones in the presence of silver(I) salt promoters gave the corresponding O-peracylated 1',5'-anhydro-D-glycitol-spiro-[1',5]-4-imino-2,2-disubstituted-1,3-dioxolanes. The D-galacto configured starting compounds furnished both spiro epimers, while the D-gluco counterparts yielded only configurationally inverted products. Under acidic conditions, O-perbenzoylated α-D-gluco-heptulopyranosonamide and ketones yielded the protected 1',5'-anhydro-D-glucitol-spiro-[1',5]-2,2-disubstituted-oxazolidin-4-ones, which were O-debenzoylated by the Zemplén protocol. These compounds had no inhibition against rabbit muscle glycogen phosphorlyase b.
authors.affiliation: Department of Organic Chemistry, University of Debrecen, POB 20, H-4010 Debrecen, Hungary.
authors.forename: András
authors.initials: A
authors.lastname: Páhi
authors.affiliation: Department of Organic Chemistry, University of Debrecen, POB 20, H-4010 Debrecen, Hungary.
authors.forename: Katalin
authors.initials: K
authors.lastname: Czifrák
authors.affiliation: Department of Inorganic and Analytical Chemistry, University of Debrecen, POB 21, H-4010 Debrecen, Hungary.
authors.forename: Katalin E
authors.initials: KE
authors.lastname: Kövér
authors.affiliation: Department of Organic Chemistry, University of Debrecen, POB 20, H-4010 Debrecen, Hungary. Electronic address: somsak.laszlo@science.unideb.hu.
authors.forename: László
authors.initials: L
authors.lastname: Somsák
mesh_terms: D000215:Acylation; D000577:Amides / Q000737:chemistry*; D000818:Animals; D004791:Enzyme Inhibitors / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D011817:Rabbits; D012997:Solvents / Q000737:chemistry*; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000577:Amides; D004791:Enzyme Inhibitors; D006027:Glycosides; D007659:Ketones; D012997:Solvents; D013141:Spiro Compounds
keywords: 4-Imino-1,3-dioxolanes; Anomeric spirocycles; Oxazolidin-4-ones; Solvent incorporation; Spiro compounds