title: Ceric ammonium nitrate-catalyzed azidation of 1,2-anhydro sugars: application in the synthesis of structurally diverse sugar-derived morpholine 1,2,3-triazoles and 1,4-oxazin-2-ones.
abstract: Azidation of 1,2-anhydro sugars with NaN(3) in CH(3)CN by using a catalytic amount of ceric ammonium nitrate has been accomplished in a regio- and stereoselective manner. Various 1,2-anhydro sugars produced 2-hydroxy-1-azido sugars in good yields which, in turn, were converted to structurally diverse sugar-derived morpholine triazoles and sugar oxazin-2-ones. These sugar derivatives were tested against various commercially available glycosidases, and two of them were found to be active in the micromolar range.
authors.affiliation: Department of Chemistry, Indian Institute of Technology, Kanpur-208 016, India.
authors.forename: Y Suman
authors.initials: YS
authors.lastname: Reddy
authors.forename: A P John
authors.initials: AP
authors.lastname: Pal
authors.forename: Preeti
authors.initials: P
authors.lastname: Gupta
authors.forename: Alafia A
authors.initials: AA
authors.lastname: Ansari
authors.forename: Yashwant D
authors.initials: YD
authors.lastname: Vankar
mesh_terms: D002241:Carbohydrates / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D002563:Cerium / Q000737:chemistry*; D015394:Molecular Structure; D009025:Morpholines / Q000737:chemistry*; D010078:Oxazines / Q000138:chemical synthesis / Q000737:chemistry*; D014230:Triazoles / Q000138:chemical synthesis*
chemical_list: D002241:Carbohydrates; D009025:Morpholines; D010078:Oxazines; D014230:Triazoles; D002563:Cerium; C037574:morpholine; C004653:ceric ammonium nitrate