INVESTIGADORES
LITTER marta Irene
artículos
Título:
Anomalous Reaction of D-Gluconamide with Benzoyl Chloride in Anhydrous Pyridine
Autor/es:
J.O. DEFERRARI; R. M DE LEDERKREMER; M.I. LITTER
Revista:
CARBOHYDRATE RESEARCH
Editorial:
ELSEVIER SCI LTD
Referencias:
Lugar: Amsterdam; Año: 1970 vol. 14 p. 103 - 107
ISSN:
0008-6215
Resumen:
The reaction of d-gluconamide with benzoyl chloride and pyridine gave a complex mixture from which ethyl or methyl 2,3,5,6-tetra-O-benzoyl-d-gluconate (5 and 6) crystallized after treatment with ethanol or methanol, respectively. These esters were formed by alcoholysis of 2,3,5,6-tetra-O-benzoyl-d-glucono-1,4-lactone (4), which was isolated by column chromatography, together with penta-O-benzoyl-d-glucononitrile (7), penta-O-benzoyl-d-gluconamide (8), N-benzoyl-penta-O-benzoyl-d-gluconamide (9), and benzamide when an excess of benzoyl chloride was used. The isolation of 4 and benzamide was explained by the formation and hydrolysis of a benzoylated imino-lactone intermediate (3).
