Preparation method of 2-deoxy-L-ribose

A technology of ribose and saccharene, applied in the field of preparing 2-deoxy-L-ribose, can solve the problems of large pollution, complicated operation, low yield and the like

Active Publication Date: 2014-04-02
JIANGXI SUKEER NEW MATERIAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to solve the different shortcomings of the above preparation method, such as low yield, difficult purification, cumbersome operation, and large pollution.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1 Preparation of β-bromo-L-triacetylated arabinose (II)

[0023] Acetic acid (252mL, 4.0mol) and L-arabinose (150g, 1.0mol) were mixed uniformly, then the above mixture was placed in an ice bath, and a solution of dichloromethane containing acetyl bromide (4.5mol, 364mL) was slowly added dropwise . Continue to keep stirring at 0-5°C for 4h after the addition is complete. After the reaction is completed, add 300 mL of dichloromethane to dilute, then add 300 mL of ice water to wash, the organic layer is washed with saturated sodium bicarbonate solution until no bubbles are generated, washed with 5% sodium thiosulfate solution until it is basically colorless, and dried over anhydrous sodium sulfate . After filtration, the solvent was recovered by distillation under reduced pressure to obtain a yellow solid, which was recrystallized from absolute ethanol to obtain 237.3 g of a white needle-like solid, 70%. β-bromo-L-triacetylated arabinose (Ⅱ): white needle-like so...

Embodiment 2

[0024] Example 2 Preparation of acetylated L-arabinosene (Ⅲ)

[0025] Add sodium bisulfate (36g, 0.3mol), zinc powder (9.75g, 0.15mol), copper sulfate (0.4g, 0.0025mol) and the β-bromo-L-triacetylated Arabinose (17.0g, 0.05mol), add 90.0g (5.0mol) of water dropwise and start stirring. After the addition, stir at room temperature for 2h. After the reaction was detected by TCL, 100 mL of ethyl acetate was added to the reaction liquid to dilute, filtered, the filtrate was washed twice with water, dried over anhydrous sodium sulfate, concentrated and rectified under reduced pressure to collect the fraction at 85-90°C to obtain 9.6 g of a colorless oily liquid , yield 96%, purity 99.1%.

[0026] Acetylated L-arabinose (Ⅲ): Colorless oily liquid.IR (KBr) v max 3075, 2941, 2894, 1741, 1643, 1435, 1371, 1240, 1148, 1087, 1055, 1041, 918, 896, 762cm -1 ; 1 H NMR (CDCl 3 , 400MHz), δppm : 2.08 (s, 3H), 2.08 (s,3H), 3.95-4.06 (m,2H), 4.86 (dd, 1H, J =6.0 and 5.2Hz), 5.19 (dt, 1H, ...

Embodiment 3

[0027] Example 3 Preparation of L-arabinosene (IV)

[0028] Take acetylated L-arabinose (20.0g, 0.1mol) and dissolve it in absolute ethanol (92.0g, 117mL), add potassium carbonate (0.85g, 0.008mol), stir at room temperature for 15min, after the reaction is detected by TCL, concentrate and recover Ethanol was obtained as a white solid. directly into the next reaction without purification.

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Abstract

The invention discloses a preparation method of 2-deoxy-L-ribose. The preparation method comprises the following steps: preparing beta-bromo-L-triacetyl arabinose by using L-arabinose as a starting material, acetyl bromide serving as a protecting group and a brominating reagent, adding the beta-bromine-L-tri-O-acetyl-arabinose into a reaction system containing zinc powder, sodium bisulfate, copper sulfate and water, reacting at normal temperature, and then diluting, filtering, washing, concentrating under reduced pressure and rectifying the reaction products to produce acetylated acetylated L-arabinal with the purity of larger than 99%; dissolving the acetylated acetylated L-arabinal into ethanol, adding potassium carbonate into the mixture to react, so as to generate L-arabinose olefin as an intermediate; performing hydration addition on the acetylated L-arabinal under composite catalyst action of a sulphoalkyl pyrazine sulphate-long-chain polyolefin sulfonic acid resin, so as to produce the 2-deoxy-L-ribose. The used raw materials are conventional reagents, while the reaction conditions are milder, the operation method and the post-treatment processes are simple, and the product yield and purity are relatively desirable.

Description

technical field [0001] The invention relates to the technical field of monosaccharides, in particular to a method for preparing 2-deoxy-L-ribose by using L-arabinose as an initial raw material. Background technique [0002] Nucleoside drugs are mainstream drugs for anti-AIDS (HIV), hepatitis (HBV / HCV), SARS (HCoV) and other viral diseases, such as: anti-hepatitis B virus clinical drugs Lamivudine (Lamivudine), telbivudine (Telbivudine), adefovir dipivoxil, etc. are nucleosides or nucleoside analogs. L-nucleoside drugs have developed rapidly in recent years due to their higher antiviral activity and lower cytotoxicity. 2-Deoxy-L-ribose is not only the basic structural unit of L-nucleoside analogs, but also the basic, key and decisive raw material for the production of L-nucleoside drugs. At present, no natural L-type deoxyribose has been found, so it cannot be obtained from natural sources, but can only be obtained through artificial synthesis. However, the existing synthet...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H3/08C07H1/00
CPCY02P20/55
Inventor 许招会廖维林廖婧熊斌夏剑辉
Owner JIANGXI SUKEER NEW MATERIAL
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