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  • 1
    Electronic Resource
    Electronic Resource
    Pheromone, 76. Synthese der Enantiomeren von 10-Methyldodecylacetat und 12-Methyltetradecylacetat, chiralen Pheromonkomponenten von Adoxophyes-Arten (Lepidoptera: Tortricidae) (1990)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1990 (1990), S. 829-831 
    Details
    ISSN: 0170-2041
    Keywords: Pheromones ; Adoxophyes spp. ; 10-Methyldodecyl acetate ; 12-Methyltetradecyl acetate ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Pheromones, 76. Synthesis of the Enantiomers of 10-Methyldodecyl Acetate and 12-Methyltetradecyl Acetate, Chiral Pheromone Components of Adoxophyes Species (Lepidoptera: Tortricidae)From enantiomeric (R)-(-)- and (S)-(+)-2-methylbutyl bromide (3), available by resolution of (R)-(-)-phenylglycinol amides of rac-2-methylbutanoic acid, and from enantiomeric 6-methyloctyl bromide (7) the corresponding phosphonium salts were obtained. Wittig olefination yielded the optically active methyl-branched olefinic THP ethers 12 and 13, hydrolysis, catalytic hydrogenation, and acetylation gave rise to the formation of the chiral title compounds (R)-(-)- and (S)-(+)-10-methyldodecyl acetate (1) and (R)-(-)- and (S)-(+)-12-methyltetradecyl acetate (2).
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1990199001155
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  • 2
    Electronic Resource
    Electronic Resource
    Pheromone, 95. Darstellung und Einsatz deuteriummarkierter Lepidopterenpheromone und Analoger zum Studium der Pheromonbiosynthese (1994)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1994 (1994), S. 133-143 
    Details
    ISSN: 0170-2041
    Keywords: Pheromones ; Deuterium labelled pheromones ; Lepidoptera ; Pheromones, biosynthetic precursors of ; Labelled compounds, deuterium ; Mamestra brassicae ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Pheromones, 95. - Synthesis and Application of Deuterium-Labelled Lepidoptera Pheromones and Analogues for the Study of Pheromone BiosynthesisBy deuteration of suitable alkynes with D2 and Wilkinson catalyst deuterium-labelled building blocks are obtained which can be transformed into the corresponding [D4]-, [D8]- and [D9]-labelled pheromones and pheromone analogues. These unsaturated deuterium-marked compounds can be converted into saturated [D6]- and [D8]-analogues of Lepidoptera pheromones by a second deuteration or subsequent hydrogenation. The analogues, comprising potential biosynthesis precursors of pheromones, were applied in vivo to female insects and deuterium incorporation into the final products of biosynthesis was recorded by GCMS.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199419940206
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  • 3
    Electronic Resource
    Electronic Resource
    Pheromone, 89 - Wittig-Synthese alkylverzweigter und cyclischer Analoger von (Z)-5-Decenylacetat, dem Sexualpheromon von Agrotis segetum (Lepidoptera: Noctuidae) (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 231-235 
    Details
    ISSN: 0170-2041
    Keywords: Pheromones ; (Z)-5-decenyl acetate ; Wittig reactions ; Agrotis segetum ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Pheromones, 89, - Wittig Syntheses of Alkyl-Branched and Cyclic Analogs of (Z)-5-Decenyl Acetate, the Sex Pheromone of Agrotis segetum (Lepidoptera: Noctuidae)By means of (Z)-selective Wittig olefination alkyl-branched and cyclic analogs of (Z)-5-decenyl acetate, the sex pheromone of the turnip moth, Agrotis segetum (Lepidoptera: Noctuidae), have been synthesized.
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199319930141
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  • 4
    Electronic Resource
    Electronic Resource
    Fullerene Dendrimers and Lipofullerenes with an Inherently Chiral Hexaaddition Pattern (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 1051-1059 
    Details
    ISSN: 1434-193X
    Keywords: Chirality ; Dendrimers ; Fullerenes ; Lipofullerenes ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---The facile synthesis of enantiomerically pure C3-symmetrical fullerene dendrimers all-R-fA-7, all-S-fC-8, all-R-fC-9, and all-S-fA-10, as well as lipofullerenes all-S-fA-11 and all-S-fC-12 involving an octahedral [3:3] addition pattern is described. The C3 symmetrical tris[bis(4-phenyl-2-oxazoline)methano]fullerenes 1, 2, 3, and 4 with known absolute configuration were used as precursors. The completion of the octahedral addition pattern was achieved by a threefold cyclopropanation with the dendritic 3,5-dihydroxybenzylic bromomalonate 5 and the lipophilic dioctadecyl bromomalonate 6. The absolute configurations of the precursor trisadducts were retained in the inherently chiral C3-symmetrical hexakisadducts 7-12. The structure and the isomeric purity of all hexakisadducts 7-12 were unambiguously proven by NMR spectroscopy and other techniques. Preliminary experiments with the dendritic hexakisadducts all-S-fC 8 and all-S-fA 10 revealed that these macromolecular ligands posess catalytic properties with respect to stereoselective cyclopropanations of styrene with ethyl diazoacetate.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
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  • 5
    Electronic Resource
    Electronic Resource
    Synthesis of a Biotinated Lipofullerene as a New Type of Transmembrane Anchor (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 1173-1181 
    Details
    ISSN: 1434-193X
    Keywords: Biotin ; Fullerenes ; Membranes ; Nanostructures ; Reflectometric interference spectroscopy ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -As a prototype for a new class of lipid membrane components, the lipophilic fullerene derivative (so-called lipofullerene) 1 was synthesized and characterized. This mixed [1:5]-hexakisadduct consists of ten long alkyl chains within five didodecyl malonate addends and a linker malonate carrying a (+)-biotin unit as part of an amphiphilic spacer. The malonates are attached to the fullerene core in an octahedral addition pattern, which was achieved by two successive cyclopropanation sequences with the functional precursor malonate 8 and dodecyl malonate 10. The final step of the synthesis of 1 was the attachment of activated biotin 5 with the deprotected precursor 11. Binding experiments followed by reflectometric interference spectroscopy [RIfS] proved the capability of 1 to bind specifically the protein streptavidin (SA) through the biotin unit. The amphiphilic behavior of 1 was demonstrated by Langmuir Blodgett (LB) film investigations.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
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  • 6
    Electronic Resource
    Electronic Resource
    Dendritic Mixed Hexakisadducts of C60 with a Th Symmetrical Addition Pattern (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 171-180 
    Details
    ISSN: 1434-193X
    Keywords: Dendrimers ; Fullerenes ; Macromolecular chemistry ; Template synthesis ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---The synthesis and complete characterization of dendritic hexakisadducts 8-13 of C60 with a mixed (1:5, 2:4, 3:3 and 4:2) Th symmetrical addition pattern is described. Pentakis-, tetrakis-, tris- and bisadducts 4-7 of C60 with diethyl malonate addends arranged in an incomplete octahedral addition pattern served as core building blocks. Completion of the pseudo-octahedral architecture was achieved by exhaustive cyclopropanation with first- to third-generation bromomalonate dendra 1-3 consisting of the corresponding Fréchet-type 3,5-dihydroxybenzyl alcohol subunits. This concept allows for the convergent synthesis of globular dendrimers with a variable number of dendritic malonates (1-4) and a high dendron density in good yields. The 1H and 13C NMR spectra reflect the Th symmetrical addition pattern of the products and reveal spatial interactions of inner dendron branches.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
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