title: Synthesis of new branched-chain amino sugars.
abstract: 1,3-Dipolar cycloaddition of methylideneaniline N-oxide to sugar enones is described. The addition occurred exclusively from the side opposite to the aglycone affording the corresponding alkyl alpha-D-lyxo-hexopyranosid-(2,3:5',4')-phenylisoxazolidin-4-uloses. Hydrogenation of these compounds readily yielded the corresponding alkyl 3-deoxy-3-N-phenylaminomethyl-alpha-D-talopyranoside, that were readily transformed to the acetates. The structure and conformation of the bicyclic compounds were determined by 1H NMR studies and semi-empirical molecular orbital calculations employing the AM1 method.
authors.affiliation: Departamento de Qui;mica Fundamental, Universidade Federal de Pernambuco Cidade Universitária, CCEN, 50.740-540, PE, Recife, Brazil.
authors.forename: João R
authors.initials: JR
authors.lastname: de Freitas Filho
authors.forename: Rajendra M
authors.initials: RM
authors.lastname: Srivastava
authors.forename: Waldenberg J P
authors.initials: WJ
authors.lastname: da Silva
authors.forename: Louis
authors.initials: L
authors.lastname: Cottier
authors.forename: Denis
authors.initials: D
authors.lastname: Sinou
mesh_terms: D000606:Amino Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D002236:Carbohydrate Conformation; D006571:Heterocyclic Compounds / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular / Q000379:methods; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000606:Amino Sugars; D006571:Heterocyclic Compounds