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Synthesis and characterization of 4,6-O-butylidene-N-(2-hydroxybenzylidene)-beta-D-glucopyranosylamine: crystal structures of 4,6-O-butylidene-alpha-D-glucopyranose, 4,6-O-butylidene-beta-D-glucopyranosylamine and 4,6-O-butylidene-N-(2-hydroxybenzylidene)-beta-D-glucopyranosylamine

hal.structure.identifierBioinorganic Laboratory [Bombay]
dc.contributor.authorRAJSEKHAR, Gudneppanavar
hal.structure.identifierBioinorganic Laboratory [Bombay]
dc.contributor.authorGANGADHARMATH, Umesh B.
hal.structure.identifierBioinorganic Laboratory [Bombay]
dc.contributor.authorRAO, Chebrolu P.
hal.structure.identifierInstitut de Chimie de la Matière Condensée de Bordeaux [ICMCB]
dc.contributor.authorGUIONNEAU, Philippe
hal.structure.identifierDepartment of Chemistry [Jyväskylä Univ] [JYU]
dc.contributor.authorSAARENKETO, Pauli K.
hal.structure.identifierDepartment of Chemistry [Jyväskylä Univ] [JYU]
dc.contributor.authorRISSANEN, Kari
dc.date.issued2002
dc.identifier.issn0008-6215
dc.description.abstractEn4,6-O-Butylidene-N-(2-hydroxybenzylidene)-beta-D-glucopyranosylamine was synthesized and characterized using analytical, spectral and single-crystal X-ray diffraction methods. 1H and 13C NMR studies showed the presence of the beta-anomer, which has also been confirmed by the crystal structure. The molecular structure of this compound showed the presence of the tridentate ONO ligation-core. Both precursors, 4,6-O-butylidene-alpha-D-glucopyranose and 4,6-O-butylidene-beta-D-glucopyranosylamine were characterized using single crystal X-ray diffraction. The alpha-anomeric nature of the former and beta-anomeric nature of the latter were proposed based on 1H NMR studies and were confirmed by determining the crystal structures. In addition, the crystal structure of 4,6-O-butylidene-beta-D-glucopyranosylamine revealed the C-1-N-glycosylation. In all the three molecules, the saccharide unit exhibits a 4C(1) chair conformation. In the lattice, the molecules are connected by hydrogen-bond interactions. The conformation of 4,6-O-butylidene-N-(2-hydroxybenzylidene)-beta-D-glucopyranosylamine is stabilized via an O-H...N intramolecular interaction, and each molecule in the lattice interacts with three neighboring molecules through hydrogen bonds of the type O-H...O and C-H...O.
dc.language.isoen
dc.publisherElsevier
dc.subject.enGlycosyl amines
dc.subject.enSingle-crystal X-ray diffraction
dc.title.enSynthesis and characterization of 4,6-O-butylidene-N-(2-hydroxybenzylidene)-beta-D-glucopyranosylamine: crystal structures of 4,6-O-butylidene-alpha-D-glucopyranose, 4,6-O-butylidene-beta-D-glucopyranosylamine and 4,6-O-butylidene-N-(2-hydroxybenzylidene)-beta-D-glucopyranosylamine
dc.typeArticle de revue
dc.identifier.doi10.1016/S0008-6215(02)00191-X
dc.subject.halChimie/Matériaux
bordeaux.journalCarbohydrate Research
bordeaux.page1477-1484
bordeaux.volume337
bordeaux.issue16
bordeaux.peerReviewedoui
hal.identifierhal-00719772
hal.version1
hal.popularnon
hal.audienceInternationale
hal.origin.linkhttps://hal.archives-ouvertes.fr//hal-00719772v1
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Carbohydrate%20Research&rft.date=2002&rft.volume=337&rft.issue=16&rft.spage=1477-1484&rft.epage=1477-1484&rft.eissn=0008-6215&rft.issn=0008-6215&rft.au=RAJSEKHAR,%20Gudneppanavar&GANGADHARMATH,%20Umesh%20B.&RAO,%20Chebrolu%20P.&GUIONNEAU,%20Philippe&SAARENKETO,%20Pauli%20K.&rft.genre=article


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