The chemistry of the 1-deoxynojirimycin system. Synthesis of 2-acetamido-1,2-dideoxynojirimycin from 1-deoxynojirimycin

The synthesis of 2-acetamido-1,2-dideoxynojirimycin (2-acetamido-1,2,5-trideoxy-1,5-imino- d-glucitol) by a double inversion procedure starting from 1-deoxynojirimycin is reported. The key intermediates were the selectively protected N-benzyl-1,5-dideoxy-1,5-imino-4,6- O-isopropylidene- d-mannitol, the triflate ester N-benzyl-3- O-benzyl-1,5-dideoxy-1,5-imino-4,6- O-isopropylidene-2- O-(trifluoromethylsulfonyl)- d-mannitol, and 2-azido- N-benzyl-3- O-benzyl-1,2,5-trideoxy-1,5-imino-4,6- O-isopropylidene- d-glucitol, readily obtained in a sequence from 1-deoxynojirimycin. Thus 1-deoxynojirimycin served as a synthon compatible with the basic operations of carbohydrate chemistry.