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Synthesis 1992; 1992(12): 1236-1238
DOI: 10.1055/s-1992-26347
short paper
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Use of Hydrazine Acetate as a Mild and Efficient Reagent for Anomeric Denitration of Carbohydrates

Tatsushi Toyokuni* , Shaopei Cai, Barbara Dean
  • *The Biomembrane Institute and University of Washington, 201 Elliott Ave. W., Seattle, Washington 98 119, USA
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Publication Date:
29 April 2002 (online)

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Treatment of 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α,β-D-galactopyranosyl nitrate (1), 3,6-di-O-acetyl-2-azido-2-deoxy-4-O-(2,3,4, 6-tetra-O-acetyl-β-D-galactopyranosyl)-α,β-D-glucopyranosyl nitrate (3), and 6-O-acetyl-2-azido-2-deoxy-3,4-O-isopropylidene-α,β-D-galactopyranosyl nitrate (5) with a slight excess of hydrazine acetate in anhydrous dimethylformamide at room temperature for 2 hours gave the corresponding hemiacetals, 2, 4, and 6 in the range of an 87-92 % yield.