A new procedure for the synthesis of azasugars

Article abstract of DOI:10.1016/0040-4039(93)88084-V

Reaction of the commercially available 2,3,5-tri-O-benzyl-D-arabinose with a primary amine (RNH₂) affords the arabinofuranosylamine 2, which on treatment with a Grignard reagent stereoselectively gives the aminoalcohol 3. 3 is an useful precursor of azasugars: it is converted into the pyrrolidine 4 by treatment with Tf₂O-Py, whereas by oxidation with PCC it affords the lactam 5 which can be reduced to the corresponding amine 6.