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A number of natural and synthetic analogues of homoazasugars, known in the literature, are promising glycosidase inhibitors. The methodologies used for the synthesis of piperidine homoazasugars are: (i) intramolecular reductive amination, (ii) intermolecular double reductive amination, (iii) amino/amido mercuration, (iv) intramolecular nucleophilic substitution, (v) synthesis from non-carbohydrate building block and aza-heterocycles and (vi) enzyme catalyzed intramolecular reductive amination. Homoazasugars showed higher selectivity and potency in the glycosidase inhibitory activity. In this report, natural occurrence, synthetic methodologies and potential application to glycosidase inhibitory activity of homoazasugars will be reviewed.

Piperidine homoazasugars: Natural occurrence, synthetic aspects and biological activity study