Abstract An optimized method for the synthesis of an important chiral scaffold,(3S, 4R, 5R)-1- N-Boc-3, 4-isopropylidene-3, 4, 5-trihydroxypiperidine, was developed. Using this intermediate, the preparation of various chiral aminodihydroxypiperidines and their transformation into a series of non-glycosidic, six-membered azanucleosides was accomplished. NMR conformation analysis of the prepared piperidine azanucleosides ...