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Preparation of diamino pseudodisaccharide derivatives from 1,6-anhydro-beta-D-hexopyranoses via aziridine-ring cleavage
Kroutil J, Budesínský M.
Jazyk angličtina Země Nizozemsko
- MeSH
- aminocukry chemická syntéza chemie MeSH
- aziridiny chemie MeSH
- financování organizované MeSH
- galaktosa analogy a deriváty chemie MeSH
- glukosa analogy a deriváty chemie MeSH
- hexosy chemie MeSH
- konformace sacharidů MeSH
- magnetická rezonanční spektroskopie MeSH
- mannosa analogy a deriváty chemie MeSH
- molekulární struktura MeSH
- sacharidové sekvence MeSH
- stereoizomerie MeSH
Twelve positional isomers of diamino pseudodisaccharide derivatives with gluco-gluco configuration have been prepared using aziridine-ring cleavage of epimino derivatives of 1,6-anhydro-beta-D-hexopyranoses of the D-allo, D-manno, and D-galacto configuration by 2-, 3-, and 4-amino derivatives of 1,6-anhydro-beta-D-glucopyranose. The N-substitution of the aziridine ring by a 2-nitrobenzenesulfonyl group and ionic-liquid solvent (N-methylpyridinium tosylate) was used to obtain cleavage products in high yield (64-93%). The cleavage reactions proceeded according to the Fürst-Plattner rule and only trans-diaxial stereoisomers were formed.
Department of Organic and Nuclear Chemistry Charles University Prague 128 43 Prague 2 Czech Republic
Citace poskytuje Crossref.org
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- $a Department of Organic and Nuclear Chemistry, Charles University in Prague, 128 43 Prague 2, Czech Republic. kroutil@natur.cuni.cz
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- $a Twelve positional isomers of diamino pseudodisaccharide derivatives with gluco-gluco configuration have been prepared using aziridine-ring cleavage of epimino derivatives of 1,6-anhydro-beta-D-hexopyranoses of the D-allo, D-manno, and D-galacto configuration by 2-, 3-, and 4-amino derivatives of 1,6-anhydro-beta-D-glucopyranose. The N-substitution of the aziridine ring by a 2-nitrobenzenesulfonyl group and ionic-liquid solvent (N-methylpyridinium tosylate) was used to obtain cleavage products in high yield (64-93%). The cleavage reactions proceeded according to the Fürst-Plattner rule and only trans-diaxial stereoisomers were formed.
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