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  • 1
    Electronic Resource
    Electronic Resource
    Synthesen biologisch wichtiger Kohlenhydrate, 27. Totalsynthese und Konfigurationsbestimmung -verzweigter 2,3,6-Tridesoxyhexosen (1981)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 114 (1981), S. 2669-2680 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Syntheses of Biologically Important Carbohydrates, 27. Total Synthesis and Determination of the Configuration of -Branched 2,3,6-Trideoxy HexosesAfter cis-hydroxylation of DL-trans-3-methyl-3-tosylamino-4-hexenal ethylene acetal (3a-4a) followed by hydrolysis, glycosidation and acetylation the anomeric forms of the methyl 4-0-acetyl-2,3,6-trideoxy-3-C-methyl-3-tosylamino-DL-hexopyranosides with lyxo- (α-14, β-15) and xylo-configuration (α-16, β-17) are obtained. Detailed spectroscopical investigations with 14-17 and with (3R)- (21) and (3s)-methyl-4-0-benzoyl-2,3,6-trideoxy-3-C-methyl-α-D-erythro-hexo-pyranoside (22) respectively, show relationships between 1H NMR parameters and the configurations at the branching point.
    Notes: Nach cis-Hydroxylierung von DL-trans-3-Methyl-3-tosylamino-4-hexenal-ethylenacetal (3a, 4a) werden nach Hydrolyse, Glycosidierung und Acetylierung die anomeren Methyl-4-O-acetyl- 2,3,6-tridesoxy-3-C-methyl-3-tosylamino-DL-hexopyranoside mit lyxo- (α-14, β-15) und xylo-Konfiguration (α-16, β-17) getrennt erhalten. Detaillierte spektroskopische Untersuchungen an 14-17 und an (3R)- (21) bzw, (3s)-Methyl-4-0-benzoyl-2,3,6-tridesoxy-3-C-methyl-α-D-erythro-hexopyranosid (22) führen zu Zusammenhängen zwischen 1H—NMR-Parametern und den Konfigurationen am Verzweigungsort.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19811140802
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  • 2
    Electronic Resource
    Electronic Resource
    Synthesen biologisch wichtiger Kohlenhydrate, 20. N-Acetyl-1,4-di-O-acetyl-β-DL-vancosamin (1979)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 112 (1979), S. 3273-3281 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Syntheses of Biologically Important Carbohydrates, 20. N-Acetyl-1,4-di-O-acetyl-β-DL-vancosamineClaisen rearrangement of 1-methyl-2-butenyl vinyl ether (3) yields trans-3-methyl-4-hexenal (4), the ethylene acetal 5 of which is aminated with selenium and chloramine T forming a mixture of the 3-methyl-3-tosylamino- (6) and 3-methyl-6-tosylamino derivatives 7. After detosylation of 6 and N-acetylation trans-3-acetylamino-3-methyl-4-hexenal ethylene acetal (9) is cis-hydroxylated to give 10/11. Cleavage of the protecting group at C-1 and peracetylation gives n-acetyl-1,4-di-O-acetyl-β-DL -vancosamine (13). The constitution of 13 is proved by mass spectrometry and the lyxo-configuration is assigned with high probability on the basis of 1 H NMR investigation *).
    Notes: Die Claisen-Umlagerung von (1-methyl-2-butenyl)-vinyl-ether (3)liefert trans-3-Methyl-4-hexenal(4), dessen Ethylenacetal 5 mit Selen und Chloramin-T zu den 3-Methyl-3-tosylamino-(6) und 3-Methl-6-tosylamino-Derivaten 7 aminiert wird. Nach Detosylierung von 6 und N-Acetylierung wird trans-3-Acetylamino-3-methyl-4-hexenal-ethylenacetal (9) zu 10/11 cis-hydroxyliert. Abspaltung der Schutzgruppe an C-1 und Peracetylierung liefert n-Acetyl-1,4-di-O-acetyl-β-DL-vancosamin (13), dessen Konstitution durch MS bewiesen und dessen lyxo-Konfiguration durch 1 H-NMR-Untersuchungen weitgehend gesichert wird *).
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19791120922
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  • 3
    Electronic Resource
    Electronic Resource
    Antibiotikamodelle, 4. Verbesserte Synthese von N-Tosyldaunosamin (1982)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 115 (1982), S. 256-260 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Antibiotic Models, 41,2). Improved Synthesis of N-TosyldaunosamineBy a large scale synthesis N-tosyldaunosamine (13) - a stable derivative of the antibiotica carbohydrate daunosamine - can now be produced in amounts of 10 g starting from cheap noncarbohydrate precursors.
    Notes: Eine neue large-scale-Synthese des N-Tosyldaunosamins (13) gestattet es, diese Depotverbindung des Antibiotika-Zuckers Daunosamin aus billigen Nicht-Kohlenhydrat-Vorstufen im 10-g-Maßstab herzustellen.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19821150125
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