Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 1, Issue 19, Pages 3321-3326Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b307455b
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A new synthetic strategy has been devised to access a variety of polyhydroxylated piperidines belonging to the azasugar class of glycosidase inhibitors. The key precursor (3aR, 7aR)-5-benzyl- 2,2-dimethyl-7-methylenehexahydro[ 1,3] dioxo[4,5-c] pyridine is obtained by photoinduced electron transfer ( PET) cyclization of the corresponding alpha-trimethylsilylmethylamine radical cation to the tethered acetylene functionality. The new molecules have been evaluated for inhibitory properties for certain beta-glycosidases and have been found to be moderate to weak inhibitors of the enzymes under study.
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