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A kind of amylose chiral stationary phase and preparation method thereof

A technology of chiral stationary phase and amylose, applied in chemical instruments and methods, other chemical processes, etc., to achieve the effects of stable structure, high selectivity, and large bonding capacity

Active Publication Date: 2018-07-20
NANJING FANHAI YILONG BIOCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, one of the biggest shortcomings of all chiral stationary phases is that not all types of chiral compounds can be separated on the same chiral chromatographic column, which means that the broad spectrum of chiral stationary phases has certain limitations

Method used

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  • A kind of amylose chiral stationary phase and preparation method thereof
  • A kind of amylose chiral stationary phase and preparation method thereof
  • A kind of amylose chiral stationary phase and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0035] Example 1: Taking silica gel-bonded amylose-(4-chlorophenylcarbamate) chiral stationary phase (CSP1) as an example

[0036] The present embodiment proposes a kind of preparation method of amylose chiral stationary phase, comprises the following steps:

[0037] The first step is to take a 1L double-necked round-bottom flask and then vacuumize it and then blow it with nitrogen. Weigh the amylose (10g) that has been vacuum-dried at 100°C and add it to the flask, then add 500mL of anhydrous N,N-dimethylethane Amide (DMA), heated to 80°C and stirred overnight. After cooling to room temperature, under a nitrogen atmosphere, anhydrous lithium chloride (21 g, 0.50 mol) and N-bromosuccinimide (NBS, 5.5 g, 31 mmol) were successively added to the flask, and reacted at room temperature for 12 h. After the reaction finished, the reaction solution was poured into 5L methanol for precipitation, filtered, and vacuum-dried to obtain the product 6-bromoamylose (12.1g, yield 87%); its re...

Embodiment 2

[0052] Example 2: Taking silica gel-bonded amylose-(3,5-dimethylphenylcarbamate) chiral stationary phase (CSP2) as an example

[0053] The present embodiment proposes a kind of preparation method of amylose chiral stationary phase, comprises the following steps:

[0054] Step 1: Take a 1L double-necked round-bottom flask and evacuate it first, then ventilate it with nitrogen gas. Weigh the amylose (15g) dried in vacuum at 100°C and add it into the flask, then add 600mL of anhydrous DMA, heat up to 80°C and stir overnight. . After cooling to room temperature, under a nitrogen atmosphere, anhydrous LiCl (47 g, 1.11 mol) and NBS (32.9 g, 0.185 mol) were successively added to the flask, and reacted at room temperature for 12 h. After the reaction, the reaction solution was poured into 8L of methanol for precipitation, filtered, and vacuum-dried to obtain the product 6-bromoamylose.

[0055] In the second step, the first step product 6-bromoamylose (7g) was added to a 1L two-neck...

Embodiment 3

[0062] Example 3: Taking silica gel-bonded amylose-(4-chloro-3-methylphenylcarbamate) chiral stationary phase (CSP3) as an example

[0063] The present embodiment proposes a kind of preparation method of amylose chiral stationary phase, comprises the following steps:

[0064] In the first step, take a 2L double-necked round-bottom flask, first vacuum and then nitrogen, weigh the amylose (21g) that has been vacuum-dried at 100°C and add it to the flask, then add 1.4L of anhydrous DMA, and heat up to 80°C overnight Stir. After cooling to room temperature, under nitrogen atmosphere, anhydrous LiCl (77.1 g, 1.82 mol) and NBS (92.5 g, 0.52 mol) were successively added to the flask, and reacted at room temperature for 12 h. After the reaction, the reaction solution was poured into 25L of methanol for precipitation, filtered, and vacuum-dried to obtain the product 6-bromoamylose.

[0065] In the second step, the first step product 6-bromoamylose (15g) was added to a 2L two-necked f...

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Abstract

The invention relates to the technical field of polysaccharide-based chiral stationary phases, and discloses a method for preparing a chiral stationary phase of triazolyl bonding amylose and a derivative thereof from silica gel through a click reaction. The chiral stationary phase of bonding-type amylose and the derivative thereof is prepared by conducting selective modification on an amylose 6-hydroxyl group and conducting alkynylation treatment on silica gel and utilizing an efficient catalyst. Due to the fact that amylose and the derivative thereof have highly ordered spatial structures and inherent chiral environments, the chiral stationary phase shows excellent resolution capacity on various chiral racemates in a liquid chromatogram and can be applied to the field of various chiral chromatographic column packing materials.

Description

technical field [0001] The invention relates to an amylose chiral stationary phase and a preparation method thereof, in particular to a kind of alkynyl functionalized silica gel, azide amylose and its derivatives through a click reaction to prepare an amylose chiral stationary phase . The chiral stationary phase can be applied to chromatographic analysis and separation of various chiral drugs, and belongs to the technical field of chromatographic separation of chiral racemates. Background technique [0002] For many years, since the physical and chemical properties of various enantiomers of organic compounds are exactly the same, but their pharmacological properties are very different, it has been a research hotspot for researchers to find a simple and accurate method for analyzing chiral compounds one. Among the many chiral drug preparation methods that have been developed, high performance liquid chromatography (HPLC) is the most commonly used analytical method for chira...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J20/29B01J20/30
CPCB01J20/29B01J2220/54B01J2220/80
Inventor 王欢欢吴瑛
Owner NANJING FANHAI YILONG BIOCHEM TECH CO LTD
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