A NEW APPROACH TO 1-DEOXY-AZASUGARS - ASYMMETRIC ASYMMETRIC-SYNTHESISOF 1-DEOXYMANNOJIRIMYCIN AND 1-DEOXYALTRONOJIRIMYCIN

A concise and flexible method, based upon the kinetic resolution of ra cemic alpha-furfuryl amine derivatives, for the asymmetric synthesis o f 1-deoxy-azasugars is described, (-)-1-Deoxymannojirimycin 1a has bee n synthesized in nine steps (5.8% overall yield) from the alpha-furfur ylamine derivative 3 and its enantiomer (+)-1-deoxymanndjirimycin 1b h as been similarly synthesized in nine steps (3.7% overall yield) from (S)-3, (-)- and (+)-1-Deoxyaltronojirimycin, 16a and 16b, have also be en synthesized in five steps (overall yields 21.5% and 25.4%, respecti vely) from the intermediates 9a and 9b, respectively.