Utilization of nosylepimines of 1,6-anhydro-beta-D-hexopyranoses for the preparation of halogenated aminosaccharides.
The aziridine ring cleavage of N-nosylepimines 3 and 7 having D-allo and D-manno configurations with halides led regioselectively to N-o-nitrobenzenesulfonylated 2-halo-3-amino- and 3-halo-2-amino-2,3-dideoxy derivatives of 1,6-anhydro-beta-D-glucopyranose 8-14 in 59-81% yields. Removal of o-nitrobenzenesulfonyl protecting group with benzenethiol afforded aminosaccharides, which were converted into more stable hydrochlorides 15-18.
Kroutil
Jirí
J
Department of Organic Chemistry, Charles University, 128 43 Prague 2, Czech Republic. kroutil@natur.cuni.cz
Karban
Jindrich
J
Budesínský
Milos
M
D000606:Amino Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D001388:Aziridines / Q000737:chemistry; D001557:Benzenesulfonates / Q000737:chemistry; D002855:Chromatography, Thin Layer; D003500:Cyclization; D005947:Glucose / Q000031:analogs & derivatives* / Q000737:chemistry*; D006219:Halogens / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009578:Nitrobenzenes / Q000737:chemistry; D010636:Phenols / Q000737:chemistry; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry
D000606:Amino Sugars; D001388:Aziridines; D001557:Benzenesulfonates; D006219:Halogens; D009578:Nitrobenzenes; D010636:Phenols; D013438:Sulfhydryl Compounds; C014989:1,6-anhydro-beta-glucopyranose; C042983:thiophenol; D005947:Glucose