328533-53-5

Upstream product

• 328533-51-3 benzoyl 6-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-α-D-mannofuranoside 
• 57492-90-7 1-O-benzoyl-2,3-O-isopropylidene-α-D-mannofuranoside 
• 328533-52-4 benzoyl 6-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-5-O-methyl-α-D-mannofuranoside 

Downstream Products

• 328533-55-7 benzoyl 6-(tert-butoxycarbonyl)amino-6-deoxy-2,3-O-isopropylidene-5-O-methyl-α-D-mannofuranoside 
• 328533-54-6 benzoyl 6-azido-6-deoxy-2,3-O-isopropylidene-5-O-methyl-α-D-mannofuranoside 
• 328533-73-9 Benzoic acid (3aS,4R,6R,6aS)-6-((R)-2-methanesulfonyloxy-1-methoxy-ethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl ester 

Relevant academic research and scientific papers

Fragmentation of carbohydrate anomeric alkoxy radicals. Synthesis of polyhydroxy piperidines and pyrrolidines related to carbohydrates

Imino sugars of the piperidine and pyrrolidine types can be specifically obtained when protected 5-amino-5-deoxyfuranopentoses, 5-amino-5-deoxyfuranohexoses, 6-amino-6-deoxyfuranohexoses, and 6-amino-6-deoxypyranohexoses undergo a tandem alkoxy radical β-fragmentation-intramolecular cyclization reaction. The reaction is promoted by the system: iodosylbenzene - iodine under mild conditions. The tert-butoxycarbonyl, benzyloxycarbonyl, and diphenylphosphinoyl radicals have been studied as amino-protecting groups. Using this methodology, polyhydroxylated pyrrolidines of the D-erythrofuranoses 34 and 35, D-threofuranose 36, L-xylofuranose 42, and D-arabinofuranose 43 series and polyhydroxylated piperidines of the D-arabinopyranose type 37 and 38 were obtained.