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 SN2 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.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry