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  • 4-acetoxy-2-azetidinone  (2)
  • Inorganic Chemistry  (2)
  • resolution  (2)
  • 1
    Electronic Resource
    Electronic Resource
    Optical Resolution of [2,2]Paracyclophanes by High-Performance Liquid Chromatography on Tris(3,5-dimethylphenylcarbamates) of Celllulos and Amylose (1990)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 123 (1990), S. 841-845 
    Details
    ISSN: 0009-2940
    Keywords: Resolution, optical / Stationary phase, Chiral / Anylose carbamates / Celluslose carbamates / [3.2]Paracyclophanes, functionalized ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Optical resolution of 22 [2,2]paracyclophane derivatives was examined by high-performance liquid chromatography (HPLC) using tris(3,5-dimethylphenylcarbamates) of cellulose and amylose as chiral stationary phases. Most compounds were completely separated into enantiomers at least on one of the stationary phases. The preparation of hte new cyclophane derivatives 10, 11, 12, 14, 16, and 19 as wel as a new procedure for the synthesis of 4-fluoro-[2,2]paracyclophane (3) are described.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19901230432
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    Paper (German National Licenses)
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  • 2
    Electronic Resource
    Electronic Resource
    Nitro- und Allyloxy-substituierte helicale [2.2]Metacyclophane: Synthese, Circulardichroismus und Röntgen-Kristallstrukturanalysen (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 1585-1590 
    Details
    ISSN: 0009-2940
    Keywords: Charge transfer ; Circular dichroism ; Helical molecules ; [2.2]Metacyclophanes ; Structure-chiroptic relationships ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Nitro- and Allyloxy-Substituted Helical [2.2]Metacyclophanes: Synthesis, Circular Dichroism and Crystal StructuresThe preparations of the title compound 3a, intraannularly nitro-functionalized, of the extraannularly substituted reference compound 3b, and of the sulfone 4 are described. Enantiomeric resolution of these helical phanes was accomplished on (+)-PTrMA and cellulose tris(3,5-dimethylphenyl)carbamate by HPLC. Racemization of the enantiomers of 3b is faster than that of the previously reported extraannularly substituted phanes. The crystal structure of 3a as well as that of the allyl ether 3d show severe distortions of the benzene rings; the CD spectrum of 3a is pointing at an intramolecular charge-transfer complex, an effect that cannot be evaluated from the CD spectrum of 3b.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911240719
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    Paper (German National Licenses)
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  • 3
    Electronic Resource
    Electronic Resource
    Optical resolution of β-lactams on 1-phenylethylcarbamates of cellulose and amylose (1992)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 4 (1992), S. 122-124 
    Details
    ISSN: 0899-0042
    Keywords: 4-acetoxy-2-azetidinone ; antibiotics ; carbapenem ; HPLC ; chiral stationary phases ; cellulose tris(1-phenylethylcarbamate) ; amylose tris(1-phenylethylcarbamate) ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Optical resolution of six β-lactams was examined by HPLC using chiral stationary phases consisting of tris((R)-, (RS)-, and (S)-1-phenylethylcarbamate)s of cellulose and amylose. All β-lactams were optically resolved at least by one of the carbamates. Amylose tris((S)-1-phenylethylcarbamate) showed high optical resolving abilities for some β-lactams.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530040210
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    Paper (German National Licenses)
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  • 4
    Electronic Resource
    Electronic Resource
    HPLC enantioseparation on cellulose tris(3,5-dimethylphenylcarbamate) as a chiral stationary phase: Influences of pore size of silica gel, coating amount, coating solvent, and column temperature on chiral discrimination (1996)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 8 (1996), S. 446-451 
    Details
    ISSN: 0899-0042
    Keywords: chiral stationary phase ; enantioseparation ; resolution ; chiral recognition ; high-performance liquid chromatography ; cellulose tris(3,5-dimethylphenylcarbamate) ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Cellulose tris(3,5-dimethylphenylcarbamate) (CDMPC) was coated on large-pore silica gels and used as a chiral stationary phase (CSP) for high-performance liquid chromatographic separation of enantiomers. The influences of pore size of silica gel, coating amount of CDMPC, coating solvent, and column temperature on chiral discrimination were investigated. CSPs prepared with a large-pore silica gel having a small surface area showed higher chiral recognition. The amount of CDMPC adsorbed on the silica gel influenced the chiral recognition of some racemates. Loading capacity of racemates increased with an increase of the amount of CDMPC supported on the silica gel, and a CSP coated with 45% CDMPC by weight can be used for both analytical and semi-preparative scale separations. The CDMPC, coated using acetone as the coating solvent, exhibited, in many cases, higher enantioselectivity than that obtained with tetrahydrofuran F as the coating solvent. © 1996 Wiley-Liss, Inc.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
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    Paper (German National Licenses)
  • 5
    Electronic Resource
    Electronic Resource
    Enantioseparation on 4-halogen-substituted phenylcarbamates of amylose as chiral stationary phases for high-performance liquid chromatography (1997)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 9 (1997), S. 63-68 
    Details
    ISSN: 0899-0042
    Keywords: enantioseparation ; chiral stationary phase ; HPLC ; amylose phenylcarbamate ; chiral discrimination ; resolution ; enantiomer ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Four 4-halogen-substituted phenylcarbamate derivatives of amylose were prepared and their chiral recognition abilities as chiral stationary phases (CSPs) for high-performance liquid chromatography (HPLC) were evaluated and compared with those of the corresponding cellulose derivatives. The amylose derivatives with fluoro, chloro, bromo, or iodo group at the four-position on the phenyl group were found to show higher chiral resolving ability than the corresponding cellulose derivatives. Among four amylose derivatives 4-fluoro- and 4-chlorophenylcarbamates showed an excellent chiral recognition ability. Especially, amylose tris(4-chlorophenylcarbamate) resolved (±)-1,2,2,2-tetraphenylethanol with a very high α value (α = 8.29). In order to obtain useful information concerning the chiral recognition mechanism of this resolution, we also performed enantioseparation of a variety of analogous racemic alcohols, and found that both the hydroxy and bulky triphenylmethyl groups of the racemate are essential for the effective chiral recognition. Chirality 9:63-68, 1997. © 1997 Wiley-Liss, Inc.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
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    Paper (German National Licenses)
  • 6
    Electronic Resource
    Electronic Resource
    Optical resolution of β-lactams by chiral HPLC on tris(phenylcarbamate)s of cellulose and amylose (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 216-222 
    Details
    ISSN: 0899-0042
    Keywords: 4-acetoxy-2-azetidinone ; antibiotics ; carbapenem ; chiral stationary phases ; cellulose tris(phenylcarbamate) ; amylose tris(3,5-dimethylphenylcarbamate) ; CD spectra ; absolute configuration ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Separation and optical resolution of 6 diastereomers and 25 racemates of β-lactams were examined by HPLC on chiral stationary phases composed of six cellulose and one amylose tris(phenylcarbamate) derivatives. Most β-lactams were optically resolved at least by one of the derivatives. The absolute configuration of β-lactams was estimated by CD spectroscopy.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530010307
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    Paper (German National Licenses)
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