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Statements

Subject Item
n2:RIV%2F61389030%3A_____%2F12%3A00382209%21RIV13-AV0-61389030
rdf:type
n6:Vysledek skos:Concept
dcterms:description
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.
dcterms:title
Alkyloxycarbonyl group migration in furanosides Alkyloxycarbonyl group migration in furanosides
skos:prefLabel
Alkyloxycarbonyl group migration in furanosides Alkyloxycarbonyl group migration in furanosides
skos:notation
RIV/61389030:_____/12:00382209!RIV13-AV0-61389030
n6:predkladatel
n7:ico%3A61389030
n3:aktivita
n12:Z n12:I n12:P
n3:aktivity
I, P(LH11048), Z(AV0Z40550506), Z(AV0Z50380511)
n3:cisloPeriodika
33
n3:dodaniDat
n15:2013
n3:domaciTvurceVysledku
n4:5112079 n4:8956723 n4:9244816
n3:druhVysledku
n17:J
n3:duvernostUdaju
n10:S
n3:entitaPredkladatele
n14:predkladatel
n3:idSjednocenehoVysledku
121694
n3:idVysledku
RIV/61389030:_____/12:00382209
n3:jazykVysledku
n20:eng
n3:klicovaSlova
Alkyloxycarbonyl group; Carbonate; Desilylation
n3:klicoveSlovo
n11:Alkyloxycarbonyl%20group n11:Desilylation n11:Carbonate
n3:kodStatuVydavatele
GB - Spojené království Velké Británie a Severního Irska
n3:kontrolniKodProRIV
[24BA331174F6]
n3:nazevZdroje
Tetrahedron
n3:obor
n18:DK
n3:pocetDomacichTvurcuVysledku
3
n3:pocetTvurcuVysledku
5
n3:projekt
n19:LH11048
n3:rokUplatneniVysledku
n15:2012
n3:svazekPeriodika
68
n3:tvurceVysledku
Pohl, Radek Dvořáková, Marcela Přibylová, Marie Migaud, M. E. Vaněk, Tomáš
n3:wos
000306618400008
n3:zamer
n8:AV0Z40550506 n8:AV0Z50380511
s:issn
0040-4020
s:numberOfPages
11
n16:doi
10.1016/j.tet.2012.05.117