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Preparation method of thioglycoside compound

A technology of thioglycosides and compounds, which is applied in the field of preparation of thioglycoside compounds, can solve the problems of complex treatment of thioglycoside compounds and cumbersome operation steps, and achieve the goal of avoiding harm to human health and the environment and simple post-processing work Effect

Active Publication Date: 2012-08-08
济南尚博生物科技有限公司
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Problems solved by technology

In addition, the follow-up treatment of the preparation of thioglycoside compounds by using boron trifluoride ether and ethanethiol is also relatively complicated, requiring multiple extractions, and finally neutralizing the solution to adjust the pH value, and the operation steps are relatively cumbersome

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  • Preparation method of thioglycoside compound
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  • Preparation method of thioglycoside compound

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preparation example Construction

[0024] The embodiment of the present invention discloses a preparation method of a thioglycoside compound, comprising the following steps:

[0025] a) dissolving the haloacetylated sugar compound and thiourea in the first organic solvent, and reacting under heating conditions to obtain the halogenated S-glycosylisothiourea;

[0026] b) The S-glycosylisothiourea halide reacts with haloethane in a mixed solution of a second organic solvent and an organic amine to obtain a thioglycoside compound.

[0027] Step a) is the reaction of the haloacetylated sugar compound with thiourea to obtain the intermediate product S-glycosylisothiourea halide. The above-mentioned first organic solvent is used as a reaction medium, and here only plays the role of a solvent, and it does not react with the raw materials as a reaction medium. The above-mentioned first organic solvent is preferably acetonitrile, dichloromethane or ethyl acetate, more preferably acetonitrile. The above reaction can on...

Embodiment 1

[0032] a) Add 162ml of 33wt% acetic acid / HBr solution to 160g tetraacetyl-L-arabinose, stir to make it dissolve, react for about 1.5h, test the reaction process by TLC spot plate; the reaction is considered complete when the raw material point disappears; Add 500ml dichloromethane in the reaction solution, add the Na of 5wt% again 2 CO 3 200ml of the solution was used to neutralize the pH value to 7, and the organic phase was separated by stirring. The organic phase was dried with anhydrous sodium sulfate and evaporated to dryness at 40°C to obtain bromotetraacetyl-L-arabinose with a yield of 639g;

[0033] b) Add the above 165g of bromotetraacetyl-L-arabinose to 630ml of acetonitrile to dissolve it, and heat it to 60°C; slowly add 36.5g of thiourea to the reaction solution, when the reflux starts, white flocs are formed ; After adding thiourea, react for about 30 minutes and test the reaction process with TLC spot plate until the raw material spots disappear; after the react...

Embodiment 2

[0036] a) Add 478ml of 33wt% acetic acid / HBr solution to 450g tetraacetyl-L-arabinose, stir to make it dissolve, react for about 1.5h, test the reaction process by TLC spot plate; the reaction is considered complete when the raw material point disappears; then Add 1.5L dichloromethane in the reaction solution, add the Na of 5wt% again 2 CO 3 600ml of the solution was used to neutralize the pH value to 7, and the organic phase was separated by stirring. The organic phase was dried with anhydrous sodium sulfate and evaporated to dryness at 40°C to obtain bromotetraacetyl-L-arabinose with a theoretical yield of 480g.

[0037]b) Add 480g of the above-mentioned bromoacetylated sugar compound into 1.86L of acetonitrile to dissolve it, and heat it to 75°C; slowly add 107.6g of thiourea to the reaction solution, and white flocs will form when the reflux begins; After adding urea, react for about 30 minutes and test the reaction progress with TLC spot plate until the raw material spot...

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Abstract

The invention provides a preparation method of a thioglycoside compound. The preparation method comprises the following steps of: (a) dissolving halogenated acetylated sugar and thiourea into a first organic solvent and reacting under a heating condition to obtain S-glycosyl isothiourea halide; and (b) reacting the S-glycosyl isothiourea halide and halothane in mixed solution of a second organic solvent and organic amine to obtain the thioglycoside compound. In the entire reaction process, the thiourea and the halothane are mainly selected and used as reactants, ethanethiol with offensive odor and toxicity is not required to be selected and used, and the hazard caused to human health and environment is effectively avoided. In addition, according to the method provided by the invention, an obtained product is extremely easy to separate crystals, the pH is not required to be adjusted, and the post-treatment operation is simple.

Description

technical field [0001] The invention relates to the field of sugar compounds, in particular to a preparation method of thioglycoside compounds. Background technique [0002] Carbohydrates are a general term for a class of compounds that contain polyhydroxy aldehydes or polyhydroxy ketones and can generate polyhydroxy aldehydes or polyhydroxy ketones after hydrolysis. Carbohydrates are the most widely distributed and most abundant organic compounds in nature, one of the components of food, and the direct product of photosynthesis of green plants. Carbohydrates account for about 3 / 4 of biological substances in nature, and all of them contain carbs from bacteria to higher animals. At the same time, carbohydrate compounds are also the main source of energy required by organisms to maintain life activities, the basic raw materials for the synthesis of other compounds, and the main structural components of organisms. Therefore, carbohydrates are one of the most important organic...

Claims

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Application Information

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IPC IPC(8): C07H1/00C07H5/10
Inventor 江成真张文岺刘顶王武宝
Owner 济南尚博生物科技有限公司
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