Artículos de revistas
Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: effect of a conformationally armed (superarmed) glycosyl donor
Fecha
2013-10-18Registro en:
Della Felice, Franco; Rúveda, Edmundo; Stortz, Carlos Arturo; Colombo, María Inés; Differential O-3/O-4 selectivity in the glycosylation of N-dimethylmaleoyl-protected hexosamine acceptors: effect of a conformationally armed (superarmed) glycosyl donor; Elsevier; Carbohydrate Research; 380; 18-10-2013; 167-173
0008-6215
Autor
Della Felice, Franco
Rúveda, Edmundo
Stortz, Carlos Arturo
Colombo, María Inés
Resumen
An assessment of the relative O-3/O-4 reactivities of both -methyl glycosides of N-dimethylmaleoyl (DMM) glucosamine and allosamine acceptors protected at O-6 with a benzyl group using a -glucopyranosyl conformationally armed donor (superarmed donor) counterpart is presented. The glycosylation of glucosamine derivatives followed the trends already observed for disarmed donors. On the other hand, the glycosylation of allosamine derivatives gave exclusively substitution on the equatorial O-4, in spite that with a disarmed donor the point of substitution is exclusively on the more hindered, electronically-preferred O-3. The glycosylation of glucosamine derivatives followed the trends already observed for disarmed donors. On the other hand, the glycosylation of allosamine derivatives gave exclusively substitution on the equatorial O-4, in spite that with a disarmed donor the point of substitution is exclusively on the more hindered, electronically-preferred O-3.