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Beta-cyclodextrin derivative and preparation method thereof, and polyurea-bond cyclodextrin chiral stationary phase prepared from beta-cyclodextrin derivative

A chiral stationary phase and cyclodextrin technology, applied in chemical instruments and methods, other chemical processes, bulk chemical production, etc., can solve the problems of low chemical stability, poor water resistance, short service life, etc., and achieve chemical stability Good performance, good batch reproducibility and low cost

Active Publication Date: 2014-07-09
广州研创生物技术发展有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] However, studies have found that single-bonded cyclodextrin chiral stationary phase materials have problems such as low chemical stability, poor water resistance, and short service life.

Method used

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  • Beta-cyclodextrin derivative and preparation method thereof, and polyurea-bond cyclodextrin chiral stationary phase prepared from beta-cyclodextrin derivative
  • Beta-cyclodextrin derivative and preparation method thereof, and polyurea-bond cyclodextrin chiral stationary phase prepared from beta-cyclodextrin derivative
  • Beta-cyclodextrin derivative and preparation method thereof, and polyurea-bond cyclodextrin chiral stationary phase prepared from beta-cyclodextrin derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] (1) Preparation of β-cyclodextrin derivatives

[0052] S1. Preparation of seven substituted 6-iodo-6-deoxy-β-cyclodextrins

[0053] Add 1 g β-cyclodextrin, 2 g iodine and 2 g triphenylphosphine in sequence to 50 mL DMF, stir and react at 90 °C for 8 h under nitrogen protection; after the reaction is stopped, add acetone to the reaction liquid to precipitate precipitate, filter The solid was collected and dried to give a light brown product.

[0054] S2. Preparation of seven-substituted 6-azido-6-deoxy-β-cyclodextrin:

[0055] Weigh 1 g of the obtained solid of S1 and 1 g of sodium azide, dissolve it in 50 mL of DMF, and react with stirring at 60 °C for 8 h under the protection of nitrogen. After the reaction was completed, 200 mL of ice water was added to precipitate a white precipitate, which was filtered, washed with water 2 to 3 times, and dried to obtain the product.

[0056] S3. Preparation of hepta-substituted 6-azido-6-deoxy-3, 5-dimethylphenylcarbamoylated β-...

Embodiment 2

[0063] (1) Preparation of β-cyclodextrin derivatives

[0064] S1. Preparation of seven substituted 6-iodo-6-deoxy-β-cyclodextrins

[0065] Add 1 g β-cyclodextrin, 4 g iodine and 4 g triphenylphosphine in sequence to 60 mL DMF, stir and react at 100 °C for 6 h under nitrogen protection; after the reaction stops, add acetone to the reaction solution to precipitate a precipitate, filter The solid was collected and dried to give a light brown product.

[0066] S2. Preparation of seven-substituted 6-azido-6-deoxy-β-cyclodextrin:

[0067] Weigh 1 g of the obtained solid of S1 and 2 g of sodium azide, dissolve it in 50 mL of DMF, and react with stirring at 70 °C for 7 h under the protection of nitrogen. After the reaction was completed, 200 mL of ice water was added to precipitate a white precipitate, which was filtered, washed with water 2-3 times, and dried in vacuo to obtain the product.

[0068] S3. Preparation of hepta-substituted 6-azido-6-deoxy-3, 5-dimethylphenylcarbamoyla...

Embodiment 3

[0075] (1) Preparation of β-cyclodextrin derivatives

[0076] S1. Preparation of seven-substituted 6-iodo-6-deoxy-β-cyclodextrin:

[0077] Add 1 g β-cyclodextrin, 5 g iodine and 5 g triphenylphosphine in sequence to 70 mL DMF, and stir the reaction at 110 °C for 6 h under the protection of nitrogen; Solid, which yielded a light brown product after drying in vacuo.

[0078] S2. Preparation of seven-substituted 6-azido-6-deoxy-β-cyclodextrin:

[0079] Weigh 1 g of the obtained solid of S1 and 2.5 g of sodium azide, dissolve it in 50 mL of DMF, and stir the reaction at 80 °C for 6 h under the protection of nitrogen. After the reaction, add 200 mL of ice water to precipitate a white precipitate, filter, wash with water 2-3 times, and dry in vacuo.

[0080] S3. Preparation of hepta-substituted 6-azido-6-deoxy-3, 5-dimethylphenylcarbamoylated β-cyclodextrin:

[0081] 1 g of the product obtained from S2 was dissolved in 70 mL of pyridine, 8 g of 3,5-dimethylphenylisocyanate was a...

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Abstract

The invention discloses a beta-cyclodextrin derivative and a preparation method thereof and a polyurea-bond cyclodextrin chiral stationary phase prepared from the beta-cyclodextrin derivative. The beta-cyclodextrin derivative has a molecular formula of [((CH3)2C6H3NHCO)14C42H49O28)(N3)7] and has a structural formula as shown in a formula (I) which is described in the specification. The beta-cyclodextrin derivative is used as a chiral selector and undergoes a Staudinger reaction with ammoniated silica gel so as to obtain the novel poly-bonded cyclodextrin chiral stationary phase. The chiral stationary phase provided by the invention has good stability in a mobile phase with strong polarity and high water content, has good selectivity with regard to chiral compounds and can be applied in high performance liquid chromatography (HPLC), simulated moving bed chromatography (SMB), supercutical fluid chromatography (SFC), etc.

Description

technical field [0001] The invention belongs to the technical field of β-cyclodextrin chiral stationary phase, in particular to a seven-substituted 6-azido-6-deoxy-3,5-dimethylphenylcarbamoylated β-cyclodextrin derivative and The preparation method thereof and the polyurea bond cyclodextrin chiral stationary phase prepared therefrom. Background technique [0002] Chirality is an essential property of nature. The enantiomers of chiral drugs have significantly different effects in vivo, and their pharmacological activities, metabolic processes and toxicity are significantly different. Therefore, the separation, purity detection and drug efficacy research of chiral drugs are getting more and more attention from the pharmaceutical industry and scientific researchers. In the past two decades, cyclodextrin chiral stationary phase high-performance liquid chromatography (HPLC) technology has been developed rapidly, and it has been widely used in the separation and preparation of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/16C08G83/00B01J20/29
CPCY02P20/54
Inventor 章伟光林纯范军
Owner 广州研创生物技术发展有限公司
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