Highly chemoselective reduction of 2,5-dinitro-1,4:3,6-dianhydro-D-glucitol with titanium(III) tetrahydroborates: Efficient synthesis of isomerically pure 2- and 5-nitro-1,4:3,6-dianhydro-D-glucitols

Article abstract of DOI:10.1055/s-1994-25631

It has been found that the reduction of 2,5-dinitro-1,4:3,6-dianhydro-D-glucitol (1) with titanium(III) tetrahydroborate (2) (- 78 → 0 °C) affords exclusively 2-nitro-1,4:3,6-dianhydro-D-glucitol (3). On the other hand, reduction of dinitrate 1 with diisopropoxytitanium(III) tetrahydroborate (4) (- 78 → 0 °C) yields 5-nitro-1,4:3,6-dianhydro-D-glucitol (5) as the only product.