title: Selective reduction of anomeric azides to amines with tetrathiomolybdate: synthesis of beta-D-glycosylamines.
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.
authors.affiliation: Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, Karnataka, India.
authors.forename: Perali Ramu
authors.initials: PR
authors.lastname: Sridhar
authors.forename: Kandikere Ramaiah
authors.initials: KR
authors.lastname: Prabhu
authors.forename: Srinivasan
authors.initials: S
authors.lastname: Chandrasekaran
mesh_terms: D000588:Amines / Q000737:chemistry*; D000617:Aminoglycosides / Q000138:chemical synthesis*; D001386:Azides / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D008982:Molybdenum / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000588:Amines; D000617:Aminoglycosides; D001386:Azides; D006027:Glycosides; D008982:Molybdenum; C020809:tetrathiomolybdate