Synthesis of aminocyclopentanols: α-d-galacto configured sugar mimics

Abstract

Four aminocyclopentanols, as mimics of putative intermediates in the hydrolysis of α-D-galactosides, have been synthesized through a number of stereoselective transformations using the cis-fused cyclopentane-1,4-lactone (1R, 5S, 7R, 8R)-7,8-dihydroxy-2-oxabicyclo[3.3.0]oct-3-one 1 as a chiral building block. The compounds were tested towards various glycosidases but showed no anomer selectivity in the inhibition of α- and β-galactosidases.