N-Aryl-O-glycosyl Haloacetimidates as Glycosyl Donors

Kurzanzeige
dc.contributor.authorHuchel, Uschideu
dc.contributor.authorTiwari, Pallavi
dc.contributor.authorSchmidt, Richard R.
dc.date.accessioned2011-06-06T07:43:53Zdeu
dc.date.available2011-06-06T07:43:53Zdeu
dc.date.issued2010deu
dc.description.abstractReaction of 1-O-unprotected tetra-O-acetyl- and tetra-O-benzyl-glucopyranose with N-aryl haloacetimidoyl chlorides in the presence of sodium hydride and 15-crown-5 afforded N-aryl-O-glucopyranosyl haloacetimidates. Mainly the β-anomers were obtained in this anomeric O-acylation-type reaction. The glycosyl donor properties of these haloacetimidates were investigated with 6-O- and 4-O-unprotected glucopyranosides as acceptors. The results were compared with those obtained with the corresponding O-glucopyranosyl trichloroacetimidates as glycosyl donors and the same acceptors. It was found that N-(2-chloro-6-methylphenyl)-O-glucopyranosyl trifluoroacetimidates (16Ad, 16Bd) exhibit glycosyl donor properties closely related to those of the corresponding N-unsubstituted O-glucopyranosyl trichloroacetimidates (12A, 12B).eng
dc.description.versionpublished
dc.identifier.citationFirst publ. in: Journal of Carbohydrate Chemistry 29 (2010), 2, pp. 61-75, DOI: 10.1080/07328301003597673deu
dc.identifier.doi10.1080/07328301003597673
dc.identifier.ppn345466241deu
dc.identifier.urihttp://kops.uni-konstanz.de/handle/123456789/13595
dc.language.isoengdeu
dc.legacy.dateIssued2011-06-06deu
dc.rightsterms-of-usedeu
dc.rights.urihttps://rightsstatements.org/page/InC/1.0/deu
dc.subjectCarbohydratesdeu
dc.subjectGlycosidationdeu
dc.subjectN-Aryl-O-glycosyl haloacetimidatesdeu
dc.subjectSynthesisdeu
dc.subjectO-Imidoylationdeu
dc.subject.ddc540deu
dc.titleN-Aryl-O-glycosyl Haloacetimidates as Glycosyl Donorseng
dc.typeJOURNAL_ARTICLEdeu
dspace.entity.typePublication
kops.citation.bibtex
@article{Huchel2010NAryl-13595,
  year={2010},
  doi={10.1080/07328301003597673},
  title={N-Aryl-O-glycosyl Haloacetimidates as Glycosyl Donors},
  number={2},
  volume={29},
  issn={0732-8303},
  journal={Journal of Carbohydrate Chemistry},
  pages={61--75},
  author={Huchel, Uschi and Tiwari, Pallavi and Schmidt, Richard R.}
}
kops.citation.iso690HUCHEL, Uschi, Pallavi TIWARI, Richard R. SCHMIDT, 2010. N-Aryl-O-glycosyl Haloacetimidates as Glycosyl Donors. In: Journal of Carbohydrate Chemistry. 2010, 29(2), pp. 61-75. ISSN 0732-8303. eISSN 1532-2327. Available under: doi: 10.1080/07328301003597673deu
kops.citation.iso690HUCHEL, Uschi, Pallavi TIWARI, Richard R. SCHMIDT, 2010. N-Aryl-O-glycosyl Haloacetimidates as Glycosyl Donors. In: Journal of Carbohydrate Chemistry. 2010, 29(2), pp. 61-75. ISSN 0732-8303. eISSN 1532-2327. Available under: doi: 10.1080/07328301003597673eng
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kops.description.openAccessopenaccessgreen
kops.identifier.nbnurn:nbn:de:bsz:352-135952deu
kops.sourcefieldJournal of Carbohydrate Chemistry. 2010, <b>29</b>(2), pp. 61-75. ISSN 0732-8303. eISSN 1532-2327. Available under: doi: 10.1080/07328301003597673deu
kops.sourcefield.plainJournal of Carbohydrate Chemistry. 2010, 29(2), pp. 61-75. ISSN 0732-8303. eISSN 1532-2327. Available under: doi: 10.1080/07328301003597673deu
kops.sourcefield.plainJournal of Carbohydrate Chemistry. 2010, 29(2), pp. 61-75. ISSN 0732-8303. eISSN 1532-2327. Available under: doi: 10.1080/07328301003597673eng
kops.submitter.emailmichael.ketzer@uni-konstanz.dedeu
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source.periodicalTitleJournal of Carbohydrate Chemistry

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