The syntheses of the polyhydroxylated piperidines deoxygalactonojirimycin 2, homogalactonojirimycins 7 and 9, and other 2,6-iminoheptitol derivatives, including an analogue of L-altropyranose, are reported. 5-Azidoaldono1,4-lactones undergo chain extension to afford azido lactols by the addition of a hydroxymethyllithium species 18, generated by transmetallation of a protected stannylmethanol derivative 17. Hydrogénation results in azide reduction with subsequent intramolecular reductive amination to give piperidine ring systems. The deprotected iminogalactopyranose analogues are potent and selective a-galactosidase inhibitors. Observations on the structural features determining selectivity of inhibition of a-galactosidases over naringinase (L-rhamnosidase) are also reported. © The Royal Society of Chemistry 1999.
|Number of pages||8|
|Journal||Journal of the Chemical Society, Perkin Transactions 1|
|Publication status||Published - 1999|