A kind of method for preparing halogenated sugar under mild conditions

A technology of halogenated sugar and conditions, which is applied in chemical instruments and methods, preparation of sugar derivatives, sugar derivatives, etc., to achieve the effects of wide application range, mild reaction conditions and thorough reaction

Active Publication Date: 2022-08-05
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem to be solved by the present invention is to overcome the shortcomings of using strong acidic and highly toxic halogenating agents to prepare halogenated sugars, and provide a method for preparing halogenated sugars with simple preparation methods, mild reaction conditions and simple post-treatment

Method used

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  • A kind of method for preparing halogenated sugar under mild conditions
  • A kind of method for preparing halogenated sugar under mild conditions
  • A kind of method for preparing halogenated sugar under mild conditions

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020]

[0021] 32.80 mg (0.074 mmol) of the peracetylated glucosinolate donor represented by formula 1a was azeotroped three times with toluene, and added Molecular sieve, add 0.7 mL of dichloromethane under argon atmosphere, then add 90 μL of 1 mol / L iodine chloride solution in dichloromethane, stir at room temperature for 2 h, after the reaction is completed, filter, remove the organic solvent by vacuum distillation, the residual The product was purified by column chromatography (eluent is a mixture of petroleum ether and ethyl acetate in a volume ratio of 3:1) to obtain 23.0 mg of chloroperacetylated glucose represented by formula 1b, with a yield of 85%. The structural characterization data of the obtained product are: 1 H NMR (400MHz, CDCl 3 )δ6.37(d,J=4.0Hz,1H),5.52(dd,J=3.2,1.2Hz,1H),5.42(dd,J=10.8,3.2Hz,1H),5.25(dd,J=10.8 ,4.0Hz,1H),4.54-4.49(m,1H), 13 C NMR (400MHz, CDCl 3 )δ170.41,170.22,170.01,169.87,91.26,69.44,67.94,67.30,67.18,61.11,20.81,20.78,20.72,20....

Embodiment 2

[0023]

[0024] 41.71 mg (0.094 mmol) of the peracetylated glucosinolate donor represented by formula 1a was azeotroped three times with toluene, and added Molecular sieve, add 0.9 mL of dichloromethane under argon atmosphere, then add 110 μL of 1 mol / L iodine bromide solution in dichloromethane, stir at room temperature for 1 h, after the reaction, filter, remove the organic solvent by vacuum distillation, the residual The product was purified by column chromatography (the eluent was a mixture of petroleum ether and ethyl acetate in a volume ratio of 3:1) to obtain 33.5 mg of bromoperacetylated glucose represented by formula 2b with a yield of 78%. The structural characterization data of the obtained product are: 1 H NMR (400MHz, CDCl 3 )δ6.61(d,J=4.0Hz,1H),5.55(t,J=9.6Hz,1H), 5.16(t,J=9.6Hz,1H),4.83(dd,J=10.0,4.0Hz, 1H), 4.35-4.26(m, 2H), 4.12(d, J=10.8 Hz, 1H), 2.10(s, 3H), 2.09(s, 3H), 2.05(s, 3H), 2.03(s, 3H) ; 13 C NMR (400MHz, CDCl 3 )δ 170.57, 169.91, 169.85, ...

Embodiment 3

[0026]

[0027] 39.25 mg (0.088 mmol) of the peracetylated glucosinolate donor represented by formula 1a was azeotroped three times with toluene, and added Molecular sieves, 0.9 mL of dichloromethane was added under an argon atmosphere, and then 27.9 mg (0.11 mmol) of iodine was added, and the reaction was stirred at room temperature for 2 h. After the reaction was completed, it was filtered, and the organic solvent was removed by distillation under reduced pressure. The residue was passed through the column layer. Analysis and purification (the eluent is a mixture of petroleum ether and ethyl acetate in a volume ratio of 3:1) to obtain 37.1 mg of iodo peracetylated glucose represented by formula 3b, with a yield of 92%. The structural characterization data of the obtained product are: 1 H NMR (400MHz, CDCl 3 )δ6.99(d,J=4.4Hz,1H),5.46(t,J=9.6Hz,1H), 5.21-5.15(m,1H),4.34(dd,J=12.8,4.0Hz,1H), 4.20(dd, J=10.0, 4.4Hz, 1H), 4.11(dd, J=12.4, 2.0Hz, 1H), 4.05(ddd, J=10.4, 3.6, ...

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Abstract

The invention discloses a method for preparing halogenated sugars under mild conditions. The halogenated sugars (chlorine, bromine and iodine) can be obtained by reacting an easily prepared glucosinolate donor with a halogen element or an interhalogen compound at room temperature. . The halogen element and the inter-halogen compound described therein are iodine element, iodine bromide and iodine chloride, which are readily available commercially. This method is applicable to all kinds of pyranose and furanose. And this method has no limitation on the protecting group of the glucosinolate donor, which can be an electron withdrawing group such as acetyl group, benzoyl group, etc., or an electron donating group such as benzyl group, silicon group, etc. At the same time, the reaction can occur in various organic solvents such as dichloromethane, acetonitrile, and toluene. The preparation method of the halogenated sugar of the present invention is simple, the reaction conditions are mild, the raw materials are readily available, the application range is wide, the halogenated sugar is compatible with acid-labile groups such as isopropylidene ketal and silicon groups, and is unstable in the separation process. The halogenated sugar can be purified by removing the solvent.

Description

technical field [0001] The invention belongs to the technical field of glycoside synthesis, in particular to a method for preparing halogenated sugars under mild conditions. Background technique [0002] Carbohydrates are important structural substances, energy substances and information transmission substances in life, and play a very important role in complex life activities. In nature, carbohydrates exist in the following forms: monosaccharides, oligosaccharides, polysaccharides and glycoconjugates. However, due to the complexity and microscopic heterogeneity of their chemical structures, it is very difficult to study the relationship between the structure and function of carbohydrates. Access to unique and single carbohydrate materials is important for understanding their physical properties, biological functions and disease-related characteristics. Currently, it is still difficult to isolate carbohydrates from natural sources in acceptable purity and quantity. Theref...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H13/04C07H13/08C07H9/04C07H15/18C07H1/00
CPCC07H13/04C07H13/08C07H9/04C07H15/18C07H1/00Y02P20/55
Inventor 柴永海郭建云周华凤王金财杨静张琦
Owner SHAANXI NORMAL UNIV
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