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  • 1975-1979  (4)
  • 1
    Electronic Resource
    Electronic Resource
    Verzweigte Zucker, XV. Glycosidsynthesen der L-Streptose (1977)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 110 (1977), S. 1896-1907 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Branched-chain Sugars, XV. Glycoside Syntheses with L-StreptoseThe halogeno derivatives of the cyclic carbonates 11 a and 11 b are most suitably used in the synthesis of L-streptose β-glycosides. α-Glycosides are obtained from the benzylidene compound 20. The benzylidene group can be subsequently removed by catalytic hydrogenation. Using the glycosyl halide 16 a also α-glycosides are formed in high yields. However, it is difficult to cleave the isopropylidene group under acidic conditions. Acetylated halides of type 4 are very labile and therefore not useful in glycoside synthesis.
    Notes: Zur Herstellung β-L-glycosidischer Verknüpfungen der L-Streptose sind die Halogenide des cyclischen Carbonats 11 a und 11 b am besten geeignet. α-L-Glycosidische Verknüpfungen der L-Streptose werden am günstigsten mit der Benzylidenverbindung 20 erhalten. Die Benzylidengruppe ist anschließend hydrogenolytisch abspaltbar. Auch das Halogenid 16 a liefert hohe Anteile an α-Glycosid. Die Isopropylidengruppe ist aber schwierig sauer abspaltbar. Acetylierte Halogenide wie 4 sind wegen ihrer Empfindlichkeit zur Glycosidsynthese weniger geeignet.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19771100533
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    Paper (German National Licenses)
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  • 2
    Electronic Resource
    Electronic Resource
    Bausteine von Oligosacchariden, VI. Synthese von Streptobiosamin (1977)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 110 (1977), S. 1925-1930 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Building Units for Oligosaccharides, VI. Synthesis of StreptobiosamineA synthesis of 5-deoxy-2-O-(2-deoxy-2-methylamino-α-D-glucopyranosyl)-3-C-formyl-D-lyxofuranose (11) (D-streptobiosamine) is described. The same synthesis was repeated with the corresponding L-sugars. It leads to 5-deoxy-2-O-(2-deoxy-2-methylamino-α-L-glucopyranosyl)-3-C-formyl-L-lyxofuranose (1) (L-streptobiosamine), the disaccharide portion of streptomycin.
    Notes: Eine Synthese der 5-Desoxy-2-O-(2-desoxy-2-methylamino-α-D-glucopyranosyl)-3-C-formyl-D-lyxofuranose (11) (D-Streptobiosamin) wird beschrieben. Die gleiche Synthese wurde auch mit den entsprechenden L-Zuckern durchgeführt. Sie lieferte 5-Desoxy-2-O-(2-desoxy-2-methylamino-α-L-glucopyranosyl)-3-C-formyl-L-lyxofuranose (1) (L-Streptobiosamin), das den Disaccharidbaustein des Streptomycins darstellt.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19771100536
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    Paper (German National Licenses)
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  • 3
    Electronic Resource
    Electronic Resource
    Bausteine von Oligosacchariden, IV. Synthese des Dihydrostreptosylstreptidins (1977)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 110 (1977), S. 1908-1915 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Building Units for Oligosaccharides, IV. Synthesis of DihydrostreptosylstreptidineReaction of the streptosyl chloride 1 with the optically active heptaacetylstreptidine 2 gives the pseudo-disaccharide 3, which can be transformed into the 2,3-O-isopropylidene derivative of streptosylstreptidine (5). Condensation of the chloride 6 with 2 leads to the glycoside 7. Deblocking and hydrogenation of 7 yields the free dihydrostreptosylstreptidine 10.
    Notes: Das Streptosylchlorid 1 reagiert mit chiralem Heptaacetylstreptidin 2 zum Pseudodisaccharid 3, das in das 2,3-O-Isopropyliden-Derivat des Streptosylstreptidins (5) überführbar ist. Das Chlorid 6 kann mit 2 zum Glycosid 7 umgesetzt werden. Hieraus gelingt es, durch Deblockierungs- und Hydrierungsschritte das freie Dihydrostreptosylstreptidin 10 zu gewinnen.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19771100534
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    Paper (German National Licenses)
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  • 4
    Electronic Resource
    Electronic Resource
    Bausteine von Oligosacchariden, V. Synthese des Dihydrostreptosyl-desoxystreptamins (1977)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 110 (1977), S. 1916-1924 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Building Units for Oligosaccharides, V. Synthesis of Dihydrostreptosyl-deoxystreptamineReaction of the streptosyl chloride 1 and the streptosyl bromide 6 with the racemie mixture of the 2-deoxystreptamine derivative 2 leads to diastereoisomeric mixtures of the α-glycosidic bonded pscudo-disaccharides, which can be separated by column chromatography. Complete deblocking, affording the pseudo-disaccharides of 4-O- and 6-O-linked dihydrostreptosyl-2-deoxystreptamines 10 a and 10 b, is possible in the case of compounds 8 a and 8 b, which are protected by the benzylidene group in the streptose moiety.
    Notes: Das Streptosylchlorid 1 und das Streptosylbromid 6 reagieren mit dem racemischen 2-Desoxy-streptamin-Derivat 2 zu trennbaren Diastereomerengemischen der α-glycosidisch verknüpften Pseudodisaccharide. Im Falle der mit der Benzylidengruppe im Streptose-Teil geschützten Produkte 8 a und 8 b ist eine vollständige Entblockierung zu den Pseudodisacchariden des 4-O- und 6-O-verknüpften Dihydrostreptosyl-2-desoxystreptamins 10 a und 10 b gelungen.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19771100535
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    Paper (German National Licenses)
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