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Selective reduction of anomeric azides to amines with tetrathiomolybdate: synthesis of beta-D-glycosylamines
Authors:Sridhar Perali Ramu  Prabhu Kandikere Ramaiah  Chandrasekaran Srinivasan
Institution:Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, Karnataka, India.
Abstract:A number of beta-d-glycosyl azide derivatives undergo reduction on treatment with tetrathiomolybdate to produce the corresponding beta-d-glycosylamines exclusively without anomerization under very mild and neutral reaction conditions. Acetyl, allyl, benzoyl, and benzyl protective groups are left untouched under the reaction conditions. An exclusive selectivity in the reduction of anomeric azides is observed, while the C-2 and C-6 azides are left untouched.
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