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Method for preparing 2-deoxidation-L-ribose

A technology of ribose and arabinoside, which is applied in the field of preparation of 2-deoxy-L-ribose, can solve difficult problems such as separation and purification, and achieve the effect of easy reaction and purification conditions, cheap price, and less "three wastes"

Active Publication Date: 2011-08-17
浙江一新制药股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But use expensive or highly toxic reagents in these methods; require difficult isolation and purification

Method used

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  • Method for preparing 2-deoxidation-L-ribose
  • Method for preparing 2-deoxidation-L-ribose
  • Method for preparing 2-deoxidation-L-ribose

Examples

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Effect test

Embodiment 1

[0023] The preparation method process of 2-deoxy-L-ribose of the present invention is as follows:

[0024] 1) Preparation of 1-O-methyl-L-arabinoside

[0025] At room temperature, add L-arabinose to 4 times the mass of saturated hydrogen chloride methanol solution. The mixture was heated to 63°C-65°C under reflux for 2-4 hours, and cooled to room temperature. The solution was concentrated to 1 / 2 the original volume to give a suspension. Filter out the solid precipitate, continue to concentrate the liquid to 1 / 4 of the original volume, filter out the solid precipitate, wash all the precipitate with 0.5 times the mass of methanol, and dry to obtain 1-O-methyl-L-arabinoside, the yield 89.7%.

[0026]

[0027] R: -CH 3

[0028] 2) Preparation of 1-O-methyl-3,4-O-isopropylidene-L-arabinoside

[0029] Dissolve the 1-O-methyl-L-arabinoside obtained in the previous step in 5 times the mass of dimethylformamide (DMF), add 2 times the mass of the reaction reagent dimethoxypropa...

Embodiment 2

[0052] The preparation method process of 2-deoxy-L-ribose of the present invention is as follows:

[0053] 1) Preparation of 1-O-ethyl-L-arabinoside

[0054] At room temperature, add L-arabinose to 4 times the mass of saturated hydrogen chloride ethanol solution. The mixture was heated to 63°C-65°C under reflux for 2-4 hours, and cooled to room temperature. The solution was concentrated to 1 / 2 the original volume to give a suspension. Filter out the solid precipitate, continue to concentrate the liquid to 1 / 4 of the original volume, filter out the solid precipitate, wash all the precipitate with 0.5 times the mass of ethanol, and dry to obtain 1-O-ethyl-L-arabinoside, the yield 90.1%.

[0055]

[0056] R: -CH 2 CH 3

[0057] 2) Preparation of 1-O-ethyl-3,4-O-isopropylidene-L-arabinoside

[0058] Dissolve the 1-O-ethyl-L-arabinoside obtained in the previous step in 5 times the mass of dimethylformamide (DMF), add 2 times the mass of the reaction reagent dimethoxypropa...

Embodiment 3

[0081] The preparation method process of 2-deoxy-L-ribose of the present invention is as follows:

[0082] 1) Preparation of 1-O-n-propyl-L-arabinoside

[0083] At room temperature, add L-arabinose to 4 times the mass of saturated hydrogen chloride in n-propanol. The mixture was heated to 63°C-65°C under reflux for 2-4 hours, and cooled to room temperature. The solution was concentrated to 1 / 2 the original volume to give a suspension. Filter out the solid precipitate, continue to concentrate the liquid to 1 / 4 of the original volume, filter out the solid precipitate, wash all the precipitate with 0.5 times the mass of n-propanol, and dry to obtain 1-O-n-propyl-L-arabinoside , yield 89.5%.

[0084]

[0085] R: -CH 2 CH 2 CH 3

[0086] 2) Preparation of 1-O-n-propyl-3,4-O-isopropylidene-L-arabinoside

[0087] Dissolve the 1-O-n-propyl-L-arabinoside obtained in the previous step in 5 times the mass of dimethylformamide (DMF), add 2 times the mass of the reaction reagent...

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Abstract

The invention relates to a method for preparing 2-deoxidation-L-ribose based on L-arabinose as a raw material. The method comprises following seven steps: protection, group activation, transformation, deprotection and purification. Synthesis reaction conditions are common without high temperature and high pressure as well as supervacuum and are easy to control, and raw materials are available; in the process, acid catalysis, organic alkaline catalysis, strong acidic cation ion exchange resin, azodiisobutyronitrile catalysis, bezaldehyde and benzoic acid reduction, organic solvent extraction are carried out; the used medium is cheap and available and has no toxicity; and yield is high and cost is low, thus the preparation method is suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of deoxyribose production, in particular to a preparation method of 2-deoxy-L-ribose. Background technique [0002] Deoxyribose is an important part of DNA that expresses human genetic information, and it is also a component of certain microorganisms and coenzymes. The nucleosides formed by the combination of deoxyribose and bases have attracted people's attention as early as the 1950s and 1960s in the application of biology and medicine. In recent years, the anticancer effect of nucleoside analogs has been paid more and more attention. The enantiomers of natural and modified nucleosides have been used in medicine as antiviral agents. The reason is that nucleosides have significant anticancer effects. Viral activity, but the toxicity is lower than its enantiomer. And L-nucleoside, whether it is normal L-RNA or 2'-deoxy L-DNA, can be used to bond D-m-RNA fragments, which has been proved to be effective in an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H3/08C07H1/00
Inventor 何遂庆李爱珍施心建童成松
Owner 浙江一新制药股份有限公司
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