Synthesis and glycosidase-inhibitory activity of cyclophellitol analogues

Abstract The 6-deoxy-1,2-anhydro-analogues of cyclophellitol, 5 and 6 , have been synthesised from diol 11 via a regioselective ring opening of the cyclic sulfate 15 , an internal S N 2 reaction and hydrogenolysis. Compounds 5, 6 , cyclophellitol 1 and its diastereoisomers 2–4 were assayed for inhibitory activity against six glycosidases. Oxirane 5 was shown to possess activity towards both β-mannosidase ( A. oryzae ) and β-glucosidase (almonds) but 6 showed no significant inhibitory activity.