Alkyloxycarbonyl group migration in furanosides

M. Dvorakova, M. Pribylova, R. Pohl, M.E. Migaud, T. Vanek

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12 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)6701-6711
Number of pages11
JournalTetrahedron
Volume68
Issue number33
DOIs
Publication statusPublished - 19 Aug 2012

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    Dvorakova, M., Pribylova, M., Pohl, R., Migaud, M. E., & Vanek, T. (2012). Alkyloxycarbonyl group migration in furanosides. Tetrahedron, 68(33), 6701-6711. https://doi.org/10.1016/j.tet.2012.05.117