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Method for preparing halogenated sugar under mild conditions

A technology of halogenated sugars 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, thorough reaction and simple process

Active Publication Date: 2020-06-12
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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  • Method for preparing halogenated sugar under mild conditions
  • Method for preparing halogenated sugar under mild conditions
  • Method for preparing halogenated sugar under mild conditions

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020]

[0021] 32.80mg (0.074mmol) of the peracetylated glucosinolate donor represented by formula 1a and toluene were azeotropically boiled three times, and added Molecular sieve, add 0.7mL of dichloromethane under argon atmosphere, then add 90μL of 1mol / L iodine chloride in dichloromethane solution, stir the reaction at room temperature for 2h, after the reaction is over, filter, and remove the organic solvent by vacuum distillation. 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 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, 67.18,61.11,20.81,20.78,20.72,2...

Embodiment 2

[0023]

[0024] 41.71mg (0.094mmol) of the peracetylated glucosinolate donor represented by formula 1a and toluene were azeotropically boiled three times, and added Molecular sieve, add 0.9mL dichloromethane under argon atmosphere, then add 110μL of 1mol / L iodine bromide dichloromethane solution, stir the reaction at room temperature for 1h, after the reaction, filter, remove the organic solvent by distillation under reduced pressure, 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 structure 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 170.57,169.9...

Embodiment 3

[0026]

[0027] 39.25mg (0.088mmol) of the peracetylated glucosinolate donor represented by formula 1a and toluene were azeotropically boiled three times, and added Molecular sieve, add 0.9mL of dichloromethane under argon atmosphere, then add 27.9mg (0.11 mmol) of iodine, and stir the reaction at room temperature for 2h. After the reaction, filter, remove the organic solvent by distillation under reduced pressure, and pass the residue through the column 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 iodoperacetylated 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=10.4,3.6,2.0Hz,1H), 2.10(s,3H) ,2.10(s,3H),2.06 (s,3H),2.03(s,3H); 13 C NMR(400MHz, CDC...

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Abstract

The invention discloses a method for preparing halogenated sugar under mild conditions. The method comprises the following steps that an easily-prepared thioglycoside donor and a halogen simple substance or halogen intercompound undergo a reaction at room temperature to obtain the halogenated sugar (chlorine, bromine and iodine). The halogen simple substance or the halogen intercompound is commercial easily available iodine elementary substance, iodine bromide and iodine chloride. The method is suitable for various pyranoses and furanoses. The method has no limitation on a protecting group ofthe thioglycoside donor, and the protecting group can be an electron withdrawing group such as acetyl, benzoyl and the like, and can also be an electron donating group such as benzyl, silicon base andthe like. Meanwhile, the reaction can occur in various organic solvents such as dichloromethane, acetonitrile and methylbenzene. The preparation method of the halogenated sugar is simple, reaction conditions are mild, raw materials are easy to obtain, the application range is wide, the halogenated sugar is compatible with acid-labile groups such as isopropylidene ketal and silicon groups, and a pure product can be obtained by removing a solvent from the halogenated sugar which is not stable in the separation process.

Description

Technical field [0001] The invention belongs to the technical field of glycoside synthesis, and specifically relates to a method for preparing halogenated sugars under mild conditions. Background technique [0002] Carbohydrate compounds are important structural substances, energy substances and information transmission substances of living bodies, and they play a very important role in complex life activities. In nature, carbohydrate compounds exist in the following forms: monosaccharides, oligosaccharides, glycans and glycoconjugates. However, due to the complexity of its chemical structure and micro-uniformity, it is very difficult to study the relationship between the structure and function of carbohydrate compounds. Obtaining a unique and single carbohydrate material is very important for understanding its physical properties, biological functions and disease-related characteristics. At present, it is still difficult to separate carbohydrate compounds from natural sources ...

Claims

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Application Information

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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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