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Chemical preparation method of L-ribose

A chemical and ribose technology, applied in the field of chemical preparation of L-ribose, can solve the problems of complicated post-processing, many steps, and many by-products

Inactive Publication Date: 2014-04-09
TIANJIN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the reaction of preparing L-ribose by the above-mentioned chemical synthesis method, either the steps of the reaction are too many, and the product of each step obtained has low purity, more by-products, and the post-treatment is more complicated; or because the purity of the obtained product is relatively low, and Column separation is also required to obtain pure products, which consumes a lot of solvent and time, which leads to low synthesis efficiency

Method used

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  • Chemical preparation method of L-ribose

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Example 1: Oxidative degradation of propylidene-α-D-allofuranose

[0016] Add 6.6g of propylidene-α-D-allofuranose, 3g of sodium bicarbonate and 300ml of distilled water into a 500ml four-necked bottle equipped with a thermometer and mechanical stirring, control the temperature at 20-25°C, and add 15g of high After the addition of sodium iodate, the reaction was continued at this temperature for 100 min, followed by TLC (developing solvent: ethyl acetate:methanol=4:1). Concentrate the reaction solution under reduced pressure (not exceeding 40°C), then extract the concentrate with 200ml×4 ethyl acetate, combine the ethyl acetate solution, dry with 100g anhydrous sodium sulfate, filter and concentrate to obtain the oxidative degradation product.

Embodiment 2

[0017] Embodiment 2: the synthesis of oxime protectant

[0018] Add 20ml of chromatographically pure methanol and 2.3g of methoxyamine into a 50ml three-necked flask equipped with a thermometer, condenser and electromagnetic stirring, heat and reflux for 10min, and dropwise add a solution of oxidative degradation products (2g of oxidative degradation products+10ml of chromatographically pure Methanol), heated to reflux for 2 hours after dropping, deionized the reaction solution with 001×7 resin (hydrogen ion form) and 201×7 resin (acetate ion form) respectively, then concentrated under reduced pressure, and reconcentrated the concentrate with ether Crystallization can give light yellow needle-like crystals, which are oxime protected substances.

Embodiment 3

[0019] Embodiment 3: the removal of isopropylidene group in the oxime protectant

[0020] Add 1g of oxime protection, 30ml of acetonitrile-water solution (9:1), 0.5g of dichlorodicyanobenzoquinone into a 50ml four-neck flask equipped with a thermometer and electromagnetic stirring, react at 80°C for 4h, concentrate under reduced pressure, and use Dissolve the concentrate in 30ml of water, decolorize with 1g×2 activated carbon, and filter.

[0021] Add the above-mentioned decolorizing solution to a 50ml three-necked flask equipped with a thermometer and electromagnetic stirring, add sodium borohydride solution (0.2g sodium borohydride+5ml water) under stirring at room temperature, and follow the reaction by TLC (developing agent is chloroform:methanol:water=85 : 30: 2), after the reaction is complete, the deionization method is the same as in Example 2, and then concentrated under reduced pressure to obtain a light yellow solid, which is the deisopropylidene protected oxime.

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Abstract

The invention relates to a chemical preparation method of L-ribose. The chemical preparation method is characterized by comprising the following steps: formulating mesityl-alpha-D-furan allose, sodium bicarbonate and distilled water into a reaction system, and adding sodium periodate for reaction at a certain temperature to obtain oxidative breakdown products; heating the oxidative breakdown products with a methanol solution of methoxyamine for a reflux reaction to obtain an oxime protected object; reacting the oxime protected object and dichlorodicyanobenzoquinone with acetonitrile-aqueous solution, then adding sodium borohydride liquid for reaction to obtain a demesityl oxime protected object; then reacting the demesityl oxime protected object with a tetrahydrofuran solution of titanium trichloride to obtain the L-ribose.

Description

(1) Technical field: [0001] The invention relates to the field of organic synthetic pharmaceutical intermediates, in particular to a chemical preparation method of L-ribose. (two) background technology: [0002] In recent years, the reports on the application of L-ribose and its derivatives in medicine are increasing day by day. The reason is that L-ribose derivatives have significant antiviral activity and are less toxic than D-ribose derivatives. Nucleoside derivatives formed by some L-ribose and derivatives 2-deoxy-L-ribose and organic bases such as adenine have great application potential in the treatment of cancer, hepatitis B and other diseases, and many compounds are being developed and applied Among them, oligonucleotides modified with L-ribose moieties can also be used to design highly effective antiallergic drug molecules. Compared with D-ribose, which widely exists in natural compounds, L-ribose does not exist in nature and can only be obtained through synthetic ...

Claims

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Application Information

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IPC IPC(8): C07H3/02C07H1/00C07H1/06
Inventor 祁世波王晓清李凤娟
Owner TIANJIN POLYTECHNIC UNIV
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