Synthesis of new branched-chain amino sugars.
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.
de Freitas Filho
João R
JR
Departamento de Qui;mica Fundamental, Universidade Federal de Pernambuco Cidade Universitária, CCEN, 50.740-540, PE, Recife, Brazil.
Srivastava
Rajendra M
RM
da Silva
Waldenberg J P
WJ
Cottier
Louis
L
Sinou
Denis
D
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
D000606:Amino Sugars; D006571:Heterocyclic Compounds