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New method for synthesizing 2 - L - ribose from 2 - D - ribose

A new method, ribose technology, applied in the field of 2-L-ribose, the raw material of nucleoside drugs, can solve the problems of high toxicity of intermediate reaction reagents, and achieve the effects of high product yield, easy availability of raw materials, and cost reduction

Inactive Publication Date: 2007-10-10
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The second route has intermediate reaction reagents that are highly toxic and requires low-temperature operation, and almost every step of the reaction must be separated by columns

Method used

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  • New method for synthesizing 2 - L - ribose from 2 - D - ribose
  • New method for synthesizing 2 - L - ribose from 2 - D - ribose
  • New method for synthesizing 2 - L - ribose from 2 - D - ribose

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Experimental program
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Effect test

Embodiment 1

[0017] 1. Add 1.5 g of D-ribose into 40 ml of pyridine solution dissolved with 2.7 g of trityl chloride, stir at room temperature for 12 hours, and remove pyridine by rotary evaporation under vacuum. Separate the liquid and spin the organic phase to dryness. Additional dichloromethane was added, and then a mixture of n-hexane and dichloromethane was added dropwise into the above solution, and a white solid appeared, which was filtered by suction. Obtained 3.73g of white powdery solid, yield 95%;

[0018] 2. Dissolve 3 g of 5-trityl ribose in 45 ml of methanol. Under the condition of zero degree ice bath, 0.86 g of sodium borohydride was added in portions, and stirred overnight for 12 hours. Spin dry, add water and ethyl acetate to separate the layers, and dry the organic phase with magnesium sulfate. Then spin off the ethyl acetate to obtain a white viscous liquid;

[0019] 3. Dissolve the product obtained in step 2 in a mixed solution of 30 ml of toluene and 5 ml of triet...

Embodiment 2

[0024] 1. Add 2 g of D-ribose and 3.5 g of trityl chloride into 50 ml of pyridine solution, stir at room temperature for 10 hours, and remove pyridine by rotary evaporation under vacuum. Separate the liquid and spin the organic phase to dryness. Additional dichloromethane was added, and then a mixture of n-hexane and dichloromethane was added dropwise into the above solution, and a white solid appeared, which was filtered by suction. Obtained 4.88g of white powdery solid, yield 93%;

[0025] 2. Dissolve 3 g of 5-trityl ribose in 50 ml of ethanol. Under the condition of zero degree ice bath, 1.22 g of potassium borohydride was added in portions, and stirred overnight for 12 hours. Spin dry, add water and ethyl acetate to separate the layers, and dry the organic phase with magnesium sulfate. Then spin off the ethyl acetate to obtain a white viscous liquid;

[0026] 3. Dissolve the product obtained in step 2 in a mixed solution of 35 ml of benzene and 5 ml of triethylamine, a...

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Abstract

This invention discloses a method for synthesizing 2-L-ribose from 2-D-ribose. The method comprises: reducing furfural, oxidizing unprotected hydroxyls with PCC in dichloroethane solvent, and changing the configuration of the product. Compared with the present techniques, the method has such advantages as simple process, no need for low temperature operation or metal catalyst, abundant raw materials, high yield and reduced cost by more than 60%.

Description

【Technical field】 [0001] The invention belongs to the technical field of medicinal chemistry, in particular to a method for synthesizing common nucleoside drug raw material 2-L-ribose from 2-D-ribose. 【Background technique】 [0002] 2-L-ribose is an important raw material for the preparation of nucleosides. After a series of synthetic transformations, a series of L-configuration nucleosides have been confirmed by biological activity tests to have good antiviral activity. Recently, it has been reported in the literature that 2-L-ribose itself has a good inhibitory effect on HCV virus. There are mainly two synthetic routes in the prior art: [0003] One is the method of synthesizing L-ribose through L-xylose proposed by Actond et al., which mainly uses the change of the chiral center after the oxidation and reduction of hydroxyl to obtain the product. Its synthetic route is: [0004] [0005] The route starting material itself is L-type sugar, so the price is high, and t...

Claims

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Application Information

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IPC IPC(8): C07H3/02
CPCY02P20/55
Inventor 孟继本张晓天邹智弘庞美丽韩杰
Owner NANKAI UNIV