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  • 9,8,7,6-Tetra-O-acetyl-N-acetylneuraminic acid-γ-lactone, synthesis of  (1)
  • TPP-DEAD-HN3, reaction with 1,2:5,6-Di-O-isopropyliden-α-D-gulofuranose  (1)
  • 1
    Electronic Resource
    Electronic Resource
    Strukturelle Abwandlungen an Kohlenhydraten, 7. Mitt. (1983)
    Springer
    Monatshefte für Chemie 114 (1983), S. 1253-1258 
    Details
    ISSN: 1434-4475
    Keywords: 3-Acetylamino-3-desoxy-D-galactose, syntheses of ; TPP-DEAD-HN3, reaction with 1,2:5,6-Di-O-isopropyliden-α-D-gulofuranose
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The synthesis of the title compound from 1,2:5,6-Di-O-isopropyliden-α-D-glucofuranose (1) via 1,2:5,6-Di-O-isopropyliden-α-D-gulofuranose (4) is reported. The key-step is the introduction of the azido function into4 which is achieved by using Triphenylphosphane/Diethylazodicarboxylate/HN3.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00799940
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  • 2
    Electronic Resource
    Electronic Resource
    Strukturelle Abwandlungen anN-Acetylneuraminsäure, 4. Mitt. Transformationen am Diethyl-dithioketal desN-Acetylneuraminsäure-γ-lactons (1985)
    Springer
    Monatshefte für Chemie 116 (1985), S. 253-262 
    Details
    ISSN: 1434-4475
    Keywords: 9,8,7,6-Tetra-O-acetyl-N-acetylneuraminic acid-γ-lactone, synthesis of ; N-Acetylneuraminic acid-γ-lactone diethyldithioketale ; Sylilation with t-butyldimethylchlorosilane and TIPSiCl2 ; 6,7-Carbonate ofN-Acylneuraminic acid-γ-lactone diethyldithioketal
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Partial protection of diethyldithioketal ofN-acetylneuraminic acid-γ-lactone using one or two equivalents oft-butyldimethylchlorosilane leads to the 9-O-silyletherderivative7 and the 8,9-bis-O-silylderivative5, resp. The reaction of1 as well as7 with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane (TIPSiCl2) yields selectively the protected products4 and9. The 9,8,7,6-tetra-O-acetyl-N-acetylneuraminic acid-γ-lactone derivative3 is formed by the oxidative desulfurazation of the peracteylated form of1 (i. e.2) by means ofNBS. By reaction of5 withTPPDEAD the 6,7-carbonato compound6 arises instead of the expected 6,7-epoxyderivative. The analogous carbonate8 is formed by treating7 with bisimidazolylcarbonate.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00798461
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