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  • 1
    Electronic Resource
    Electronic Resource
    Synthesis of Acyclic Carba-Nucleoside Phosphonates, Structural Analogues to Natural Deoxyribonucleotides (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 931-936 
    Details
    ISSN: 1434-193X
    Keywords: Nucleosides ; Phosphonates ; Nucleophilic additions ; C-C coupling ; Reduction ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Acyclic carba-nucleoside phosphonates, modelled on natural deoxyribonucleotides have been prepared starting from DNA nucleobases and tert-butyl acrylate. The products obtained from a Michael-type reaction were elongated to β-oxo esters that were first reduced to β-hydroxy esters and then transformed into protected β-hydroxy aldehydes. Wittig-Horner-Emmons reaction with the anion of tetraisopropyl methylenebisphosphonate gave, after deprotection, the desired 4-hydroxy-6-purinyl- or -6-pyrimidinyl-1-hexenylphosphonic acids. A dimer, potential precursor of acyclic polynucleotides (APN), homomorphous with DNA, was also prepared.
    Type of Medium: Electronic Resource
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    Paper (German National Licenses)
  • 2
    Electronic Resource
    Electronic Resource
    Solution-Phase Synthesis of Mixed Amide Libraries by Simultaneous Addition of Functionalities (SPSAF) to a Diketopiperazine Tetracarboxylic Acid Scaffold Monitored by GC Analysis of Isobutyl Alcohol (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 1669-1675 
    Details
    ISSN: 1434-193X
    Keywords: Combinatorial chemistry ; Amides ; Gas chromatography ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---A symmetric diketopiperazine scaffold 2 has been prepared in a very simple two-step procedure from L-aspartic acid dimethyl ester. This product (a tetracarboxylic acid equally protected at the two symmetric positions) has been employed as a template for the synthesis of mixed amide libraries in the solution phase using the SPSAF (simultaneous addition of functionalities) strategy. By judicious choice of the amines employed, it is possible to prepare parallel libraries containing hundreds of products using just a small number of different amines. We have also developed a simple method for monitoring the required conversion of the acid into amides based on an assay of the amount of iBuOH (determined by GC) formed during the coupling mediated by isobutyl chloroformate. We have observed that a conversion higher than 90% (iBuOH by GC) guarantees correct formation of the desired amides. This indirect method for assessing the conversion in a combinatorial reaction employing mixed reactants (SPSAF) can conveniently be used for the routine determination of libraries prepared in the solution phase. In a broader perspective, the present results contribute as a further step in the development of new and simple systems for monitoring the progress and evolution of combinatorial reactions
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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