13C-N.M.R. characterizations of the sarsasapogenin disaccharides, the filiferins a and b: 2-O-(ß-d-xylopyranosyl)- and 2-O(ß-d-glucopyranosyl)-ß-d-galactopyranosides
Por:
Lemieux R.U., Ratcliffe R.M., Arreguin B., de Vivar A.R., Castillo M.J.
Publicada:
1 ene 1977
Resumen:
Filiferin B is identical to timosaponin A-III, which had previously been shown to be 3-O-[2-O-(?-d-glucopyranosyl)-?-d-galactopyranosyl]sarsasapogenin. A larger-scale isolation of filiferin B from the seeds of Yucca filifera led to the isolation of filiferin A, now shown to be 3-O-[2-O-?-d-xylopyranosyl)-?-d-galactopyranosyl]-sarsasapogenin. The presence of the xylose residue was established by way of hydrolysis. 8-Methoxycarbonyloctyl 2-O-(?-d-glucopyranosyl)-?-d-galactopyranoside was synthesized to serve as a model for interpretation of the 13C-n.m.r. spectrum of filiferin B. The information thus gained, together with the 13C-n.m.r. spectra of other, simple model-compounds, permitted assignment of the structure for filiferin A. 8-Methoxycarbonyloctyl 2-O-(?-d-glucopyranosyl)-?-d-galactopyranoside was also synthesized. © 1977.
Filiaciones:
Lemieux R.U.:
Department of Chemistry, University of Alberta, Edmonton, Alta. T6G 2G2, Canada
Instituto de Quimica (451), Universidad Nacional Autonoma de Mexico, Mexico 20, D.F., Mexico
Ratcliffe R.M.:
Department of Chemistry, University of Alberta, Edmonton, Alta. T6G 2G2, Canada
Instituto de Quimica (451), Universidad Nacional Autonoma de Mexico, Mexico 20, D.F., Mexico
Arreguin B.:
Department of Chemistry, University of Alberta, Edmonton, Alta. T6G 2G2, Canada
Instituto de Quimica (451), Universidad Nacional Autonoma de Mexico, Mexico 20, D.F., Mexico
de Vivar A.R.:
Department of Chemistry, University of Alberta, Edmonton, Alta. T6G 2G2, Canada
Instituto de Quimica (451), Universidad Nacional Autonoma de Mexico, Mexico 20, D.F., Mexico
Castillo M.J.:
Department of Chemistry, University of Alberta, Edmonton, Alta. T6G 2G2, Canada
Instituto de Quimica (451), Universidad Nacional Autonoma de Mexico, Mexico 20, D.F., Mexico
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