Chromatographische Enantiomerentrennung an Polysaccharidderivaten

Okamoto, Yoshio; Yashima, Eiji

doi:10.1002/(sici)1521-3757(19980420)110:8<1072::aid-ange1072>3.0.co;2-q

Cited by 87 publications

(1 citation statement)

References 256 publications

(68 reference statements)

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“…Actually, the concept of SMB chromatography was not adapted until 1990s; further the technology was transferred to the production of pharmaceuticals [7]. It is great important to develop several types of highly selective adsorbents in 1980s, the resolution is for analytical HPLC application [8], which allows precisely separation of components from complex products. In particular, the combination of HPLC methods and SMB technology with the assist of dynamic axial compression (DAC) [9], facilitates the production of large amounts of pure products.…”

Section: Process Lcmentioning

confidence: 99%

Development and Application of Liquid Chromatography in Life Sciences

Zhu¹,

Chen²

2017

J Chromatogr Sep Tech

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Liquid chromatographic approaches cover a wide range of applications today. It is closely relevant in scientific studies, which provides a powerful identification of certain components that will be effective for curing specific diseases. Especially important, LC methods can assist us for isolation and purification of therapeutic drugs that benefit for the development of medical industry. As the development of liquid chromatography, the single effective component within a drug can be separated and purified under extreme purity requirements from a biological system with great complexity and abundance. However, improvement of LC methods is still urgently needed for better application of this method to benefit our lives.

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Section: Process Lcmentioning

confidence: 99%

Development and Application of Liquid Chromatography in Life Sciences

Zhu¹,

Chen²

2017

J Chromatogr Sep Tech

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Structure/Chiroptics Relationships of Planar Chiral and Helical Molecules

Grimme¹,

et al. 1998

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Synthesis, Crystal Structure, and Circular Dichroism Spectra of (1S)-4,8-Diphenylbarbaralane-2,6-dicarbonitrile – Chiroptical Properties of the Transition State of a Degenerate Cope Rearrangement

Quast¹,

Seefelder

Peters

et al. 1999

Eur. J. Org. Chem.

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Diphenylbicyclo[3.3.1]nonane‐2,6‐dione rac‐3 is resolved in 57 % overall yield by chromatographic separation of the diastereomeric (R)‐N‐(1‐phenylethyl)carbamates 9 which are obtained from (R)‐(1‐phenylethyl) isocyanate (8) and the 6‐hydroxydiphenylbicyclo[3.3.1]nonan‐2‐ones endo‐ and exo‐4. The enantiomers (1R)‐ (e.r. = 98:2) and (1S)‐3 (e.r. = 97:3) are regenerated from 9 by reduction with lithium aluminium hydride followed by Swern oxidation of the resulting diols 5. The title compound (1S)‐1 is synthesised in three steps from (1S)‐3 in improved yield on the route that had led to rac‐1. The absolute configurations are established by X‐ray diffraction analyses of the carbamates endo‐(1R)‐9 and exo‐(1S)‐9. X‐ray diffraction analyses were also performed of the camphanoate (1R)‐7, the intermediates rac‐endo‐4 and (1S)‐3, and the title compound (1S)‐1. Hydroxy ketone rac‐endo‐4 adopts similar conformations in the solid state and in solution as shown by a comparison of vicinal 1H,1H coupling constants from proton spectra with those calculated from torsional angles in the crystal. The molecular structures of (1S)‐1 and (1S)‐3 closely resemble those of the corresponding racemates investigated previously. These results show (i) that intermolecular interactions in the solid state are of minor importance and (ii) that the unusually long C2–C8 distance of (1S)‐1 and rac‐1 (168 pm) is a molecular but not an averaged property due to a non‐degenerate Cope rearrangement in the crystal. CD spectra are reported for (1R)‐ and (1S)‐3, the unsaturated dicarbonitrile (1S)‐13, and (1S)‐1. The CD spectrum of (1S)‐1 exhibits a weak positive band at 459 nm where rac‐1 shows a temperature‐dependent absorption which has been assigned to the higher, vibronic state represented by rac‐1*. The intensity of the weak CD band depends on the temperature and the solvents in the same way as the UV/Vis absorption of rac‐1. This supports the conclusion that both bands originate from the same source, viz. the transition state 1* of the degenerate Cope rearrangement 1 ⇄ 1′.

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Chromatographische Enantiomerentrennung an Polysaccharidderivaten

Cited by 87 publications

References 256 publications

Development and Application of Liquid Chromatography in Life Sciences

Development and Application of Liquid Chromatography in Life Sciences

Structure/Chiroptics Relationships of Planar Chiral and Helical Molecules

Synthesis, Crystal Structure, and Circular Dichroism Spectra of (1S)-4,8-Diphenylbarbaralane-2,6-dicarbonitrile – Chiroptical Properties of the Transition State of a Degenerate Cope Rearrangement

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