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  • Wiley-Blackwell  (2)
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  • 1
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 68 (1985), S. 534-544 
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Spontaneous Opening of the Pyrimidine Ring of Pyrrolo[2,3-d]pyrimidines after Intramolecular AcylationPhase-transfer alkylation of 4-methoxy-2-methylthio-7H-pyrrolo[2,3-d]pyrimidine (2) with ethyl 3-bromopropionate leads regioselectively to the ester 3a. After displacement of its methylthio group and saponification of the ester function, the acid 3e is obtained which can be transferred to the functionalized deazahypoxanthine 3f by either treatment with dry HBr/glacial AcOH or by nucleophilic displacement of the 4-methoxide. Reaction of 3f with a H2O-soluble carbodiimide results in an intramolecular acylation at N(1) by the activated ester; the intermediate 4 undergoes spontaneous hydroxylation and subsequent opening of the pyrimidine ring under formation of the pyrrolo[1,2-a]pyrimidine derivative 6. Its structure was proved by X-ray analysis. Subsequent deformylation of 6 in alkaline medium leads to the compound 7 in almost quantitative yield.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1983 (1983), S. 1409-1415 
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Preparation and Determination of the Configuration of xylo- and ribo-3′-S-Alkyl Derivatives of 2′-DeoxyadenosineThe syntheses of 2′-deoxy-3′-S-ethyl- (2), 2′-deoxy-3′-S-isopropyl- (3), and 2′-deoxy-3′-S-propyl-3′-thioadenosine (4) are described. Besides the xylo isomers 2a-4a the appropriate ribo isomers 2b-4b are formed as side products with a ratio of 6:1. The xylo configuration has been correlated to the main products 2a-4a according to the X-ray analysis of 2a which established the configuration.
    Notes: Die Synthesen von 2′-Desoxy-3′-S-ethyl- (2), 2′-Desoxy-3′-S-isopropyl- (3) und 2′-Desoxy-3′-S-propyl-3′-thioadenosin (4) werden beschrieben. Neben den xylo-Isomeren 2a-4a werden die entsprechenden ribo-Isomeren 2b-4b als Nebenprodukte im Verhältnis von 6:1 gebildet. Die xylo-Konfiguration konnte den Hauptprodukten 2a-4a durch Bestimmung der Konfiguration mittels Röntgenstrukturanalyse von 2a zugeordnet werden.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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