Deoxyiminoalditols from Aldonolactones. III. Preparation of 1,4-Dideoxy-1,4-imino-L-gulitol. - Evaluation of 1,4-Dideoxy-1,4-iminoihexitols as Glycosidase Inhibitors

Article abstract of DOI:10.1016/S0040-4020(01)90479-X

2,6-Dibromo-2,6-dideoxy-D-altrono-1,4-lactone (1) was converted into a mixture of 2,3-anhydro-6-bromo-6-deoxy-D-allono-1,4- (7) and -1,5-lactone (8), which by treatment with aqueous NH3 (25percent) gave 3,6-dideoxy-3,6-imino-D-gluconic acid (9).Convertion into the 1,4-lactone 10 followed by reduction with NaBH4 gave 1,4-dideoxy-1,4-imino-L-gulitol (11). - Reduction of the dibromolactone 1 gave 2,6-dibromo-2,6-dideoxy-D-altritol (1,5-dibromo-1,5-dideoxy-D-talitol) (2) which was unstable since it was readily transformed into 3,6-anhydro-2-bromo-2-deoxy-D-altritol (3).Treatment of either 2 or 3 with aqueous NH3 (25percent) gave 1-amino-1-deoxy-3,6-anhydro-D-allitol (6). - The reaction of the bromo compounds with aqueous NH3 were followed by 13C NMR spectroscopy. - Evaluation of nine 1,4-dideoxy-1,4-iminohexitols with D- and L- allo, talo-, galacto-, ido- and with L-gulo-configurations as glycosidase inhibitors is reported.