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Simple synthesis of D-and L-deoxyribose

A deoxyribose and synthesis method technology, applied in the direction of deoxygenated/unsaturated sugar, bulk chemical production, chemical recovery, etc., can solve the problems of difficult medium-scale production or even industrialization, high toxicity, and enlarged amount of reactants, etc., to achieve The effect of cheap raw materials, convenient operation, and simple synthetic route

Inactive Publication Date: 2002-05-22
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] Because the above-mentioned D- / L-deoxyribose synthesis route also has various disadvantages, such as being difficult for medium-scale production or even industrialization; the method of reducing thiosulfonate by hydrogen radicals is very toxic and difficult to react increase in volume

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1 Synthesis of D-deoxyribose

[0034] Starting from cheap and easy-to-obtain mannitol, protected by acetonide and oxidized by sodium periodate, D-glyceraldehyde acetone can be obtained, and then highly selective propargylation reaction with zinc powder and propyne bromide is carried out to obtain The D-homopropargyl alcohol intermediate 9 was obtained in 63% overall yield. 1 Hydroxyl protection

[0035] 1.13g (6.6mmol) homopropargyl alcohol compound (9) was dissolved in THF or anhydrous DMF (2mL), TBSCl (1.35g, 8.84mmol) and imidazole 1.35g (18.35mmol) were added, and stirred at room temperature for 20 hours. Dilute and extract with 100 mL of diethyl ether, wash with distilled water (10 mL×2), saturated sodium chloride solution (10 mL) respectively, anhydrous Na 2 SO 4 dry. Filtration, concentration, and purification by column chromatography gave R=TBS product 11-11.82 g, yield 97.3%. 1 H-NMR (300MHZ, CDCl 3 ): δ0.11(3H, s), 0.14(3H, s), 0.8...

Embodiment 2

[0039] Example 2 Synthesis of D-deoxyribose

[0040]Dissolve 8 mmol of homopropargyl alcohol compound (9) in 5 mL of anhydrous THF or anhydrous CH 2 Cl 2 (3 mL), PhCOCl (10 mmol) and triethylamine (18 mmol) were added, and stirred at room temperature for 23 hours. After the reaction was finished, add saturated aqueous ammonium chloride solution, extract with 100mL dichloromethane, wash with saturated sodium chloride solution (10mL), anhydrous Na 2 SO 4 dry. Filtration, concentration, and purification by column chromatography gave the product 11-2 of R=PhCO with a yield of 98.9%.

[0041] 20.6 mmol of the substrate (11-2) was dissolved in 60 mL of anhydrous methanol, 600 mg of Lindlar catalyst and 400 μl of quinoline were added, and hydrogenated at room temperature and pressure for 4 hours. TLC showed that the reaction was complete. Suction filter with a sand core funnel covered with a layer of diatomaceous earth, concentrate, and perform column chromatograp...

Embodiment 3

[0045] The synthesis of embodiment 3 L-deoxyribose:

[0046] Starting from L-ascorbic acid, protected by acetone fork, oxidized by hydrogen peroxide, and oxidized by lead tetraacetate, L-glyceraldehyde acetone can be obtained, and then carry out highly selective propargylization reaction with zinc powder and propyne bromide to 49.2 % overall yield obtained the high propargyl alcohol intermediate 10. 1 hydroxyl protection

[0047] 2.88g (16.9mmol) homopropargyl alcohol compound (10) was dissolved in anhydrous DMF (4mL), TBSCl (3.19g, 20.9mmol) and imidazole (3.00g, 44.4mmol) were added, and stirred at room temperature for 36 hours. Diluted with ether and extracted, washed with water and saturated sodium chloride solution respectively, anhydrous Na 2 SO 4 dry. Filtration, concentration, and purification by column chromatography yielded 4.12 g of product 12-1 with R=TBS, with a yield of 86.7%. IR (KBr): 3315, 2988, 2932, 1462cm -1 .EI-MS (E / Z, %): 269 (M + -...

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PUM

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Abstract

The present invention relates to a simple high-effective synthesis method of D-and L-desoxyribose, which includes the following steps: using cheap easily-available D-high-alkyne propanol or L-high-alkyne propanol as raw material, protecting hydroxyl group, using Lindlar catalyst to make selective hydrogenation, using ozone to make oxidation according to different substituent making it react with acid, then react with alkali or react with reducing agent or lewis acid to remove protecting group and making cyclization reaction to obtain the invented product.

Description

technical field [0001] The invention provides a simple and efficient new synthesis method of D- and L-deoxyribose. Background technique [0002] D-deoxyribose is the basic unit of DNA, and it is a very important basic raw material in modern biotechnology, and its price is relatively expensive. L-deoxyribose is a non-natural sugar. Now people have realized that L-deoxyribose analogs and derivatives have important pharmacological properties, such as antiviral, antitumor activity, etc., and their toxicity is significantly reduced. In many nucleic acids today Numerous applications have been obtained in the research and synthesis of drug-like compounds. In the past, its sources were synthesized by very complicated compounds, so the price was even more expensive. Therefore, it is meaningful to develop a simple and efficient method for D- and L-deoxyribose synthesis. [0003] The synthesis method of D-deoxyribose (D-Deoxyribose) has been reported in many literatures. C.De Miche...

Claims

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Application Information

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IPC IPC(8): C07H3/08
CPCY02P20/55Y02P20/582
Inventor 胡守刚吴毓林
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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