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  • 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.
  • 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. (en)
Title
  • Alkyloxycarbonyl group migration in furanosides
  • Alkyloxycarbonyl group migration in furanosides (en)
skos:prefLabel
  • Alkyloxycarbonyl group migration in furanosides
  • Alkyloxycarbonyl group migration in furanosides (en)
skos:notation
  • RIV/61389030:_____/12:00382209!RIV13-AV0-61389030
http://linked.open...avai/predkladatel
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  • I, P(LH11048), Z(AV0Z40550506), Z(AV0Z50380511)
http://linked.open...iv/cisloPeriodika
  • 33
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  • 121694
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  • RIV/61389030:_____/12:00382209
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  • Alkyloxycarbonyl group; Carbonate; Desilylation (en)
http://linked.open.../riv/klicoveSlovo
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  • GB - Spojené království Velké Británie a Severního Irska
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  • [24BA331174F6]
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  • Tetrahedron
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  • 68
http://linked.open...iv/tvurceVysledku
  • Dvořáková, Marcela
  • Pohl, Radek
  • Vaněk, Tomáš
  • Přibylová, Marie
  • Migaud, M. E.
http://linked.open...ain/vavai/riv/wos
  • 000306618400008
http://linked.open...n/vavai/riv/zamer
issn
  • 0040-4020
number of pages
http://bibframe.org/vocab/doi
  • 10.1016/j.tet.2012.05.117
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