Čeština
EnglishAlkyloxycarbonyl group migration in furanosides.
Dvořáková M., Přibylová M., Pohl R., Migaud M.E., Vaněk T.
TETRAHEDRON 68[33]: 6701–6711, 2012
Keywords: Alkyloxycarbonyl group; Carbonate; Desilylation; Furanoside; Migration
Abstract: A migration of methyloxycarbonyl group from secondary to primary hydroxyl was observed in furanosides (ribosides and xylosides) under usual desilylation conditions using tetrabutylammonium fluoride. The migration was studied further on several alkyloxycarbonyl furanosides under either basic or acidic conditions. As follows from C labelling experiments and product distribution, the migration in xylosides, proceeds intramolecularly via six-membered cyclic carbonate, whereas in ribosides, the migration is intermolecular. Acidic conditions prevented the migration in ribosides whereas the migration in xylosides was circumvented under neutral conditions.
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IEB authors: Marcela Dvořáková, Marie Kvasnicová, Tomáš Vaněk
TETRAHEDRON 68[33]: 6701–6711, 2012
Keywords: Alkyloxycarbonyl group; Carbonate; Desilylation; Furanoside; Migration
Abstract: A migration of methyloxycarbonyl group from secondary to primary hydroxyl was observed in furanosides (ribosides and xylosides) under usual desilylation conditions using tetrabutylammonium fluoride. The migration was studied further on several alkyloxycarbonyl furanosides under either basic or acidic conditions. As follows from C labelling experiments and product distribution, the migration in xylosides, proceeds intramolecularly via six-membered cyclic carbonate, whereas in ribosides, the migration is intermolecular. Acidic conditions prevented the migration in ribosides whereas the migration in xylosides was circumvented under neutral conditions.
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