Sulfur spacer arm (R)-BIONL CSP filler and preparation method thereof

Abstract

The invention discloses a sulfur spacer (R)-BINOL CSP filler as well as a preparation method and application thereof. The structural formula of the sulfur spacer (R)-BINOL CSP is shown in the specification. In the formula, the structural formula of the silica gel carrier after hydrogen is removed is represented. The filler can separate chiral compounds of various structure types, has good stability, is suitable for being used as a high performance liquid chromatography filler, can resolve three chiral compounds of thalidomide, salbutamol and ractopamine under the condition of a polar mobile phase, has stable chiral recognition capability, and can be used as a high performance liquid chromatography filler for separating chiral compounds of thalidomide, salbutamol and ractopamine. The requirements of enantiomer separation and analysis of chiral drugs and quality control in the production and clinical use process can be met.

Description

technical field [0001] The invention relates to the technical field of filler preparation technology, in particular to a sulfur spacer arm (R)-BIONL CSP filler and a preparation method and application thereof. Background technique [0002] Biological macromolecules such as proteins, polysaccharides, nucleic acids, etc. have chirality, and chiral substances with optical activity widely exist in animals and plants. High performance liquid chromatography chiral stationary phase method (CSP method) can be used for both analytical separation and enantiomer preparation and semi-preparation due to its high efficiency and convenience, and has become a commonly used method in the separation of chiral enantiomers. CSP method It is to fix the chiral selector (CS) on the surface of the carrier through covalent bonds, physical coating or particle fixation. When the chiral drug enantiomer interacts with CS, a temporary unstable Enantiomers are separated due to different energy or stabili...

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Problems solved by technology

[0003] However, there is no CSP that can adapt to the enantiomer separation of various structural types and high enantiomer separation selectivity. The commonly used chiral stationary phases include brush CSP, cyclodextrin and its derivatives CSP, crown ether and Derivative CSP, macrocyclic antibiotic CSP, polysaccharide derivative CSP, etc., the spacer arms of these commonly used CSP are mostly urea groups, amide bonds, ester groups, carbamates, and these groups will also participate in the chiral recognition process Due to its unique catalytic effect such as high efficiency and high enantioselectivity, chiral thiourea catalysts use amino acids, binaphthol, natural products such as sugar, cinchona base, etc. as raw materials to design and synthesize new chiral sulfur Urea catalysts have obtained very high enantioselectivity (82% ~ 97% ee)

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