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Synthesis 1994; 1994(10): 1032-1034
DOI: 10.1055/s-1994-25631
short paper
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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

K. S. Ravikumar* , Srinivasan Chandrasekaran
  • *Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India and IDL-Nitro Nobel Basic Research Institute, Sankey Road, Malleswaram, Bangalore 560 003, India
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Publication Date:
27 September 2002 (online)

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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.