Alkyloxycarbonyl group migration in furanosides

0382209 - ÚEB 2013 RIV GB eng J - Journal Article
Dvořáková, Marcela - Přibylová, Marie - Pohl, Radek - Migaud, M. E. - Vaněk, Tomáš
Alkyloxycarbonyl group migration in furanosides.
Tetrahedron. Roč. 68, č. 33 (2012), s. 6701-6711. ISSN 0040-4020. E-ISSN 1464-5416
R&D Projects: GA MŠMT(CZ) LH11048
Institutional research plan: CEZ:AV0Z50380511; CEZ:AV0Z40550506
Keywords : Alkyloxycarbonyl group * Carbonate * Desilylation
Subject RIV: DK - Soil Contamination ; De-contamination incl. Pesticides
Impact factor: 2.803, year: 2012

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-13 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.
Permanent Link: http://hdl.handle.net/11104/0212498