Synthesis of 1-deoxymannojirimycin analogues using N-tosyl and N-nosyl activated aziridines derived from 1-amino-1-deoxyglucitol

Abstract 3,4;5,6-Diisopropylidene protected 1-amino-1-deoxy- d -glucitol was transformed into N -tosyl and N -nosyl activated aziridine intermediates, which underwent ring opening by reaction with various nucleophiles. The 5,6-diols resulting from selective hydrolysis of the terminal acetal group were subjected to (2-N→6-OH) cyclisation using two different methods for activation of 6-OH. Final deprotection of the N -nosyl and 3,4-acetal group proceeded smoothly to afford 6-substituted analogues of 1-deoxymannojirimycin.