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- W2145051208 abstract "N,N-Diethyl-1,2-O-isopropyliden-3,5-di-O-mesyl-α-D-glucofuranuronsäureamid (2b) reagiert mit Azid-Ionen unter SN2-Substitution und Inversion am C-5 zur L-ido-Verbindung 3. Eine Nachbargruppenreaktion der N,N-Diethylcarboxamidgruppe, wie sie beim Einsatz von Acetat-Ionen beobachtet wird, tritt nicht ein. Die Konfiguration von 3 wurde durch Röntgenstrukturanalyse bestimmt. Die Elementarzelle der Kristalle von 3 enthält zwei symmetrie-unabhängige Moleküle, die unterschiedliche Konformationen aufweisen. Der Furanosering zeigt in einem Molekül eine E4- im anderen eine 3T4-Konformation. Die Aminonitrilsynthese des D-ribo-Aldehyds 8 liefert ein 1:1-Gemisch der D-allo- und L-talo-Aminonitrile 10a und 11a. Monosaccharides Containing Nitrogen in the Ring, XXXV. Investigations into the Synthesis of 5-Amino-5-deoxyhexuronic Acids The reaction of N,N-diethyl-1,2-O-isopropylidene-3,5-di-O-mesyl-α-D-glucofuranuronamide (2b) with azide ions proceeds via an SN2 substitution with inversion at C-5 and yields the L-ido derivative 3. A neighbouring-group participation of the N,N-diethylcarboxamide group does not occur, as observed by the application of acetate ions. The configuration of 3 was determined by X-ray structure analysis. The crystals of 3 have two symmetrically independent molecules per unit, each of them having different conformations. The furanoid rings correspond with the E4 conformation and with the 3T4 conformation, respectively. The aminonitrile synthesis of the D-ribo aldehyde 8 yields a 1:1 mixture of D-allo- and L-talo-aminonitriles 10a and 11a." @default.
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- W2145051208 date "1977-06-01" @default.
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- W2145051208 title "Monosaccharide mit stickstoffhaltigem Ring, XXXV. Untersuchungen zur Darstellung von 5-Amino-5-desoxyhexuronsäuren" @default.
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- W2145051208 doi "https://doi.org/10.1002/cber.19771100613" @default.
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