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Selenium-containing compound selenium sugar, selenium glucoside and preparation method thereof

A technology for selenium compounds and glucose, which is applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., can solve the problems of complex components, difficult to obtain raw materials, and difficult separation.

Inactive Publication Date: 2017-11-14
CHENGDU LAURELSCI TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, its composition is complex, and it is difficult to obtain a single structure, which is not conducive to in-depth research on it.
There are also high-purity selenomethionine and selenocysteine ​​on the market, but the raw materials are not easy to obtain and the synthesis cost is high
[0003] In summary, the existing problems in the prior art are: due to the further metabolism of selenoamino acids formed by cultivating malt, selenium enters the protein, and the structure of the protein itself is extremely complex, diverse, unstable and difficult to separate
Or react with sodium cyanide and ammonium chloride after the addition of methyl mercaptan and acrolein to generate a-aminonitrile, and then obtain methionine through hydrolysis, which uses highly toxic sodium cyanide, and there are many synthesis steps. make it more expensive
Synthesize selenomethionine by this method, the raw material of selenocysteine ​​is not easy to obtain, and the synthesis cost is high

Method used

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  • Selenium-containing compound selenium sugar, selenium glucoside and preparation method thereof
  • Selenium-containing compound selenium sugar, selenium glucoside and preparation method thereof
  • Selenium-containing compound selenium sugar, selenium glucoside and preparation method thereof

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preparation example Construction

[0059] like figure 1 Shown, the preparation method of the selenium-containing compound that the embodiment of the present invention provides comprises the following steps:

[0060] S101: 1-bromoacetyl protecting group sugar, forms salt with various selenium-containing compounds, the temperature of forming bromine salt is 25-65°C, and then decomposes under alkaline conditions, the degradation temperature is 10-45°C, and the degradation solvent is Water: chloroform = 1:1 mixed solvent;

[0061] S102: Then use corresponding reagents to alkylate, the alkylation temperature is 35-50°C, and finally carry out transesterification and deprotection at 0-15°C to obtain the target product.

[0062] The preparation method of the selenium-containing compound that the embodiment of the present invention provides comprises:

[0063] i) reacting the corresponding bromosugar protected with a protecting group with selenourea, and then degrading it under alkaline conditions, or

[0064] ii) reac...

Embodiment 1

[0072] Example 1 Preparation of 2,3,4,6-O-tetraacetyl-α-D-glucose-1-isoselenuronium hydrobromide

[0073] Add 30ml of acetone into a 50ml three-necked flask, add 2.5g of selenourea and reflux for 30 minutes, cool down to 30°C, 10g of 2,3,4,6-O-tetraacetyl-α-D-1-bromoglucose Add the system, keep the temperature between 30-35°C, and react for 2 hours. Cool down to 0°C and stir for 40 minutes, filter, recrystallize the filter cake with acetone, filter, and dry to obtain an off-white solid. 1H NMR (DMSO-d6) δ2.02(8.91H); δ2.05(2.99H); δ3.79-3.83(t, 1.05H); δ4.07-4.11(t, 0.97H); δ4.82 -4.88(m, 2.03H); δ5.03-5.04(d, 0.99H); δ5.28-5.31(t, 1.01H); δ5.39-5.42(t, 1.01H); δ6.99(2.98 h)

Embodiment 2

[0074] Example 2 Preparation of 1-seleno-2,3,4,6-O-tetraacetyl-α-D-glucose

[0075] Add 10 grams of 2,3,4,6-O-tetraacetyl-α-D-glucose-1-isoselenuronium hydrobromide into 30ml of water and 30ml of chloroform, stir for 30 minutes, add 10 grams of sodium bicarbonate , stirred at room temperature for 5 hours. The liquid was separated, the organic layer was washed with water, dried and concentrated, and the oil was crystallized from ether to obtain a yellow-green waxy solid. 1H NMR (DMSO-d6) δ1.98-2.02(d, 11.96H); δ4.15-4.21(m, 2.01H); δ4.41-4.44(q, 1.02H); δ4.47-4.49(m , 0.99H); δ5.25-5.27(t, 1.00H); δ5.39-5.41(t, 1.00H); δ5.94-5.96(t, 1.00H)

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Abstract

The invention belongs to the technical field of selenium-containing compounds and discloses a selenium-containing compound selenium sugar, selenium glucoside and a preparation method thereof. The method comprises the following steps: using corresponding glycosyl bromide protected by a protecting group for reacting with selenourea and then degrading under an alkaline condition, or using the corresponding glycosyl bromide protected by the protecting group for directly reacting with selenium hydrogen silicate or using the corresponding glycosyl bromide protected by the protecting group for reacting with sodium selenide and potassium selenide; using the acquired raw material for reacting with a corresponding hydrocarbylation reagent or the corresponding glycosyl bromide protected by the protecting group represented by R2 or using the corresponding glycosyl bromide protected by the protecting group for directly reacting the corresponding selenol or sodium selenium alcohol and selenium potassium alcohol; and lastly, removing protection, thereby acquiring target compounds. The compound prepared according to the invention can be used for obviously improving the absorption and conversion of organism for selenium element, so that the selenium element can be utilized by a human body.

Description

technical field [0001] The invention belongs to the technical field of selenium-containing compounds, in particular to a selenium-containing compound selenosaccharide, selenoglycoside and a preparation method thereof Background technique [0002] Selenium is an essential trace element for the human body, a protective factor that can prevent nutritional liver necrosis; it is the active ingredient of glutathione peroxidase; selenium deficiency is an important cause of Keshan disease. Selenium has the effect of anti-cancer cell proliferation, can inhibit the energy metabolism of cancer cells, and can improve the immune function of cancer patients. At the same time, selenium supplementation can eliminate heavy metal ions in the body, and directly excrete heavy metals that induce cancer. It has a strong antioxidant effect, and selenium supplementation can remove garbage from the human body. However, the distribution of selenium on the earth's surface is extremely unbalanced, an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/14C07H1/00
CPCC07H1/00C07H15/14Y02P20/55
Inventor 吴继超彭开金鲁灵江郑涛高海丰罗仕忠杨久才
Owner CHENGDU LAURELSCI TECH
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