Preparation of diamino pseudodisaccharide derivatives from 1,6-anhydro-beta-D-hexopyranoses via aziridine-ring cleavage.
Twelve positional isomers of diamino pseudodisaccharide derivatives with gluco-gluco configuration have been prepared using aziridine-ring cleavage of epimino derivatives of 1,6-anhydro-beta-D-hexopyranoses of the D-allo, D-manno, and D-galacto configuration by 2-, 3-, and 4-amino derivatives of 1,6-anhydro-beta-D-glucopyranose. The N-substitution of the aziridine ring by a 2-nitrobenzenesulfonyl group and ionic-liquid solvent (N-methylpyridinium tosylate) was used to obtain cleavage products in high yield (64-93%). The cleavage reactions proceeded according to the Fürst-Plattner rule and only trans-diaxial stereoisomers were formed.
Kroutil
Jirí
J
Department of Organic and Nuclear Chemistry, Charles University in Prague, 128 43 Prague 2, Czech Republic. kroutil@natur.cuni.cz
Budesínský
Milos
M
D000606:Amino Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D001388:Aziridines / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D005690:Galactose / Q000031:analogs & derivatives / Q000737:chemistry; D005947:Glucose / Q000031:analogs & derivatives / Q000737:chemistry; D006601:Hexoses / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008358:Mannose / Q000031:analogs & derivatives / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000606:Amino Sugars; D001388:Aziridines; D006601:Hexoses; C458759:galactosan; C458739:mannosan; C014989:1,6-anhydro-beta-glucopyranose; C033132:aziridine; D005947:Glucose; D008358:Mannose; D005690:Galactose