IQUIR 05412
INSTITUTO DE QUIMICA ROSARIO
Unidad Ejecutora - UE
artículos
Título:
A comparative study of the influence of some protecting groups on the reactivity of D-glucosamine acceptors with a galactofuranosyl donor
Autor/es:
BOHN, M. L.; COLOMBO, M. I.; STORTZ, C. A.; RÚVEDA, E. A.
Revista:
CARBOHYDRATE RESEARCH
Editorial:
Elsevier
Referencias:
Año: 2006 vol. 341 p. 1096 - 1104
ISSN:
0008-6215
Resumen:
Competitive glycosylation experiments with a galactofuranosyl trichloroacetimidate donor were performed with glucosamine acceptors having a free 4-OH group and carrying different protecting groups at N-2, O-3, and O-6. The most reactive acceptor is the N-dimethylmaleimido 3,6-di-O-benzylated derivative (6c), which reacts even faster than the oxazolidinone 1a. Molecular orbital calculations have helped to rationalize these experimental facts in terms of a hardhard reaction occurring between the donor and the acceptor.
