Selective reduction of anomeric azides to amines with tetrathiomolybdate: synthesis of beta-D-glycosylamines.
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.
Sridhar
Perali Ramu
PR
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, Karnataka, India.
Prabhu
Kandikere Ramaiah
KR
Chandrasekaran
Srinivasan
S
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
D000588:Amines; D000617:Aminoglycosides; D001386:Azides; D006027:Glycosides; D008982:Molybdenum; C020809:tetrathiomolybdate