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  • 1
    Electronic Resource
    Electronic Resource
    Monosaccharide mit stickstoffhaltigem Ring, XXXVII. Synthese von 1,5-Didesoxy-1,5-imino-D-galactit (1980)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 113 (1980), S. 2601-2608 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Monosaccharides Containing Nitrogen in the Ring, XXXVII. Synthesis of 1,5-Dideoxy-1,5-imino-D-galactitolThe oxime mixture 3 + 5 of the 1,6-anhydro-furanose-5-ulose 2 can be preferably hydrogenated to the 5-amino sugar 9a with galacto-configuration. Hydrolysis of the benzyloxycarbonyl compound 9b gives the sugar 7 containing nitrogen in the pyranose ring, which yields by hydrogenation 1,5-dideoxy-1,5-imino-D-galactitol (13).
    Notes: Das Oximgemisch 3 + 5 der 1,6-Anhydro-furanos-5-ulose 2 läßt sich bevorzugt zum 5-Amino-Zucker 9a der galacto-Konfiguration hydrieren. Hydrolyse der Benzyloxycarbonyl-Verbindung 9b liefert den Zucker 7 mit Stickstoff im Ring, aus dem 1,5-Didesoxy-1,5-imino-D-galactit (13) erhältlich ist.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19801130803
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  • 2
    Electronic Resource
    Electronic Resource
    Bausteine von Oligosacchariden, LIII Synthese von 3-Desoxy-D-manno-2-octulosonsäure-(KDO-)-haltigen Trisacchariden (1984)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1984 (1984), S. 1288-1297 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Building Units of Oligosaccharides, LIII. - Synthesis of Trisaccharides Containing 3-Deoxy-D-manno-2-octulosonic Acid (KDO)The disaccharide 9 consisting of two glucosamine units reacts with the pyranosyl bromide of 3-deoxy-D-manno-2-octulosonic acid (KDO) 11 to give the KDO-containing trisaccharides 12 and 14 of which the α-glycosidically linked isomer 12 is the most preponderant product. In a series of deblocking steps the free trisaccharide α-KDO-(2→3)-β-D-GlcNAc-(1→6)-D-GlcNAc 18 could be obtained from 12. The assignment to the α-glycosidic linkage of the KDO unit in 12 has been established by converting 19 into the lactone 20.
    Notes: Durch Umsetzung des aus zwei Glucosamin-Einheiten bestehenden Disaccharides 9 mit dem Pyranosylbromid der 3-Desoxy-D-manno-2-octulosonsäure (KDO) 11 sind die KDO-haltigen Trisaccharide 12 und 14 zu erhalten, von denen das α-glycosidisch verknüpfte Produkt 12 sehr stark überwiegt. Durch eine Entblockierungssequenz ist aus 12 das freie Trisaccharid α-KDO-(2→3)-β-D-GlcNAc-(1→6)-D-GlcNAc 18 zu gewinne. Die Zuordnung zur α-glycosidischen Verknüpfung des KDO-Teiles in 12 erfolgte durch Überführung von 19 in das Lacton 20.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198419840704
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  • 3
    Electronic Resource
    Electronic Resource
    Bausteine von Oligosacchariden, LII. Synthese von Disacchariden aus 3-Desoxy-D-manno-2-octulosonsäure (KDO) und D-Glucosamin (1984)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1984 (1984), S. 1270-1287 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Building Units of Oligosaccharides, LII. - Synthesis of Disaccharides Containing 3-Deoxy-D-manno-2-octulosonic Acid (KDO) and D-GlucosamineThe pyranosyl bromide 2 of 3-deoxy-D-manno-2-octulosonic acid (KDO) can be coupled favourably with benzyl 2-benzyloxycarbonylamino-2-deoxy-4,6-O-ethyliden-α-D-glucopyranoside (7) which yields the (2→3)-glycosidically linked disaccharide containing KDO and D-glucosamine. Using mercury salts as catalysts it depends on the kind of solvent whether only the α-D-glycosidically bound product 10a or a mixture of the anomers will be obtained. After separation of the anomers and deblocking, the two disaccharides α-KDO-(1→3)-D-GlcNAc 21 and β-KDO-(2→3)-D-GlcNAc 26 have been prepared. The assignment of the anomeric configuration could be accomplished by NOE experiments and by conversion into the lactone 31.
    Notes: Das Pyranosylbromid 2 der 3-Desoxy-D-manno-2-octulosonsäure (KDO) läßt sich am günstigsten mit dem Benzyl-2-benzyloxycarbonylamino-2-desoxy-4,6-O-ethyliden-α-D-glucopyranosid (7) zu (2→3)-glycosidisch verknüpften Disacchariden aus KDO und D-Glucosamin umsetzen. Je nach Art des Lösungsmittels wird nur das α-D-glycosidisch verknüpfte Produkt 10a oder ein Gemisch der Anomeren erhalten. Quecksilbersalze dienen als Katalysatoren. Nach Trennung der Anomeren und Entblockierung wurden die beiden Disaccharide α-KDO-(2→3)-D-GlcNAc 21 und α-KDO-(2→3)-D-GlcNAc 26 dargestellt. Die Zuordnung der Anomerenkonfiguration erfolgte durch NOE-Experimente und durch Überführung in das Lacton 31.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198419840703
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