Preparation method of 2-deoxidation-D-ribose
A ribose, 24-hour technology, applied in the preparation of sugar derivatives, deoxygenated/unsaturated sugars, chemical instruments and methods, etc., can solve the problems of environmental pollution, difficult industrialization, low yield, etc., and achieve easy access to raw materials and synthetic routes Short, high-yield effects
Active Publication Date: 2014-08-27
FUJIAN RIBIO TECH CO LTD
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Problems solved by technology
[0015] This reaction utilizes mercury compounds, which will pollute the environment, and the yield is low, so it is not easy for industrialization
Method used
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Embodiment 1
[0066] The preparation of embodiment 1,2-deoxy-D-ribose
[0067] (1) Reformasky reaction
[0068]At 25°C, D-glyceraldehyde acetone (10g, 76.8mmol) and acid-washed activated zinc powder (the zinc powder was washed with 10% hydrochloric acid, water, and ethanol in sequence, and finally vacuum-dried at 40°C for 24 hours) (10g, 154mmol) was dissolved in dry tetrahydrofuran (100mL), and ethyl bromoacetate (12.8mL, 115mmol) was slowly added dropwise under nitrogen protection. After two hours of reaction, saturated ammonium chloride aqueous solution (100mL) was added, and diatom After soil filtration, the aqueous layer was washed with ethyl acetate (200mL×4), the organic layers were combined, and dried over sodium sulfate, and the solvent was removed under reduced pressure to obtain an oil, which was obtained by column chromatography (n-hexane:ethyl acetate) to obtain the formula The compound shown in Ⅰ (13.4g), the yield is 80%, ESI / MS m / z[M+H] + 219.4.
[0069] (2) hydroxyl prot...
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Abstract
The invention discloses a preparation method of 2-deoxidation-D-ribose. The method comprises the following steps: (1) carrying out a Reformasky reaction on D-glyceraldehyde acetonide and ethyl bromoacetate at an inert atmosphere and under a catalytic action of active zinc powder so as to obtain a compound shown in the formula I; (2) carrying out a substitution reaction on the compound shown in the formula I and an organic silicon protecting agent in the presence of an alkali so as to obtain a compound shown in the formula II; (3) carrying out a reduction reaction on the compound shown in the formula II under the condition of a reducing agent so as to obtain a compound shown in the formula III; (4) carrying out an oxidation reaction on the compound shown in the formula III under the condition of an oxidizing agent so as to obtain a compound shown in the formula IV; (5) carrying out deprotection on the compound shown in the formula IV in the presence of an acid and then carrying out a cyclization reaction so as to obtain the 2-deoxidation-D-ribose. According to the method, the Reformasky reaction is adopted, so that the selectivity is good; the high-yield compound shown in the formula I is obtained. The method is convenient to operate, low in raw material cost and easy to industrialize.
Description
technical field [0001] The invention relates to a preparation method of 2-deoxy-D-ribose, belonging to the field of drug synthesis. Background technique [0002] 2-Deoxy-D-ribose is a kind of monosaccharide widely used. It is the basic raw material and key intermediate of nucleoside drugs. It is mainly used to synthesize nucleoside anti-tumor and anti-viral drugs, such as zidovudine , lamivudine, and stavudine have important development value and market prospects. [0003] The synthesis methods of 2-deoxy-D-ribose mainly include: [0004] (1) Using glucose as raw material, isomerize into 3-deoxyhexose acid in alkali, then Ruff 3-deoxyhexose acid to obtain 2-deoxy-D-ribose, and finally treat with aniline. The reaction scheme is as follows: [0005] [0006] The raw material of this method is easy to obtain and the process is simple, but the purification process is cumbersome, the yield is low, and it is difficult to produce on a large scale. [0007] (2) Isomerize pent...
Claims
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IPC IPC(8): C07H3/08C07H1/00
Inventor 陈振昌张红娟
Owner FUJIAN RIBIO TECH CO LTD