Synthetic method of methyl-2,3,4-trioxy-benzyl-beta-D-pyran riboside

A ribopyranoside and synthetic method technology, which is applied in the field of organic compound synthesis and preparation, can solve problems such as environmental protection, difficulty in feeding materials, and easy to cause danger, achieve high yield, promote reaction progress, and avoid harsh requirements

Active Publication Date: 2014-10-29
济南尚博医药股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because sodium hydride is very active, it reacts violently with water and generates flammable and explosive hydrogen gas, which is very easy to cause danger
And the use of sodium hydride makes the reaction have very high requirements on air humidity. Once the air humidity is slightly high, it is difficult to feed smoothly
At the same time, benzyl bromide with strong tear gas is used. Although the activity is very high, it is very environmentally friendly and it is difficult to guarantee the working environment of workers.

Method used

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  • Synthetic method of methyl-2,3,4-trioxy-benzyl-beta-D-pyran riboside

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preparation example Construction

[0020] The invention provides a method for synthesizing methyl-2,3,4-trioxy-benzyl-β-D-ribopyranoside, comprising: combining 1-methyl-β-D-ribopyranoside and Benzyl chloride reacts under the action of potassium hydroxide and tetrabutylammonium iodide, or under the action of potassium hydroxide and tetrabutylammonium bromide, to prepare methyl-2,3,4-trioxy -Benzyl-β-D-ribopyranoside.

[0021] The present invention uses potassium hydroxide instead of sodium hydride as the base, and simultaneously adds tetrabutylammonium bromide or tetrabutylammonium iodide to successfully prepare methyl-2,3,4-trioxy-benzyl-β-D - Ribopyranoside, which avoids the risk factors caused by the use of sodium hydride and the harsh requirements on environmental humidity, so that the reaction has a higher yield.

[0022] The present invention uses 1-methyl-β-D-ribopyranoside and benzyl chloride as reaction raw materials, and there is no special requirement on the source, which can be commercially availabl...

Embodiment 1

[0036] Add 828g of toluene after dehydration to a 2L three-necked flask with a reflux condenser, and add 80g of 1-methyl-β-D-ribopyranoside under stirring. Cool the system down to room temperature, add 80g of tetrabutylammonium bromide, grind 304g of potassium hydroxide powder to 500-600 mesh, raise the temperature to reflux, then add 203g of benzyl chloride dropwise, and continue the reflux reaction for 1h after the dropwise addition. After the reaction, cool the system down to 40-50°C, wash the toluene layer with 920g*3 deionized water, collect the organic phase and concentrate under reduced pressure to a syrup with a weight loss on drying of less than 10%, and then add 2.5 times the weight of the syrup to the syrup Isohexane, cooled to below 10°C, crystallized and dried to obtain 197.2 g of methyl-2,3,4-trioxo-benzyl-β-D-ribopyranoside with a yield of 93%.

[0037] The structure of the product was characterized by proton nuclear magnetic resonance spectroscopy, the results ...

Embodiment 2

[0039] Add 1500 g of toluene after dehydration to a 2 L three-necked flask with a reflux condenser and a water separator, and add 80 g of 1-methyl-β-D-ribopyranoside under stirring. Cool the system down to room temperature, add 40g of tetrabutylammonium bromide, grind 80g of flake potassium hydroxide to 500-600 mesh, raise the temperature to 50°C, then add 450g of benzyl chloride dropwise, and continue the reflux reaction for 1h after the dropwise addition. After the reaction, the toluene layer was washed with 920g*3 deionized water, the organic phase was collected and concentrated under reduced pressure to a syrup whose lod was less than 10%, and then 2.5 times the weight of the syrup was added to the syrup. crystallized and dried to obtain 205 g of methyl-2,3,4-trioxy-benzyl-β-D-ribopyranoside with a yield of 96.6%.

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Abstract

The invention provides a synthetic method of methyl-2,3,4-trioxy-benzyl-beta-D-pyran riboside. The method comprises the following step: enabling 1-methyl-beta-D-pyran riboside and benzyl chloride to react under the actions of potassium hydroxide and tetrabutylammonium iodide or under the actions of potassium hydroxide and tetrabutylammonium bromide to prepare methyl-2,3,4-trioxy-benzyl-beta-D-pyran riboside. According to the synthetic method provided by the invention, potassium hydroxide is used for replacing sodium hydride as alkali, and tetrabutylammonium bromide or tetrabutylammonium iodide is added at the same time to successfully prepare methyl-2,3,4-trioxy-benzyl-beta-D-pyran riboside; the synthetic method can be used for avoiding risk factors caused by the application of sodium hydride and avoiding harsh requirements for the environment humidity, and ensures that the reaction has relatively high yield.

Description

technical field [0001] The invention relates to the technical field of synthesis and preparation of organic compounds, in particular to a method for synthesizing methyl-2,3,4-trioxy-benzyl-β-D-ribocopyranoside. Background technique [0002] 1-Methyl-2,3,4-trioxo-benzyl-β-D-ribopyranoside is a pharmaceutical intermediate for the preparation of 2,3,4-trioxo-benzyl-5-hydroxypentanal methyl oxime important raw materials. [0003] The method for preparing 1-methyl-2,3,4-trioxy-benzyl-β-D-ribocopyranoside in the prior art is mainly to add 1-methyl-β-D-ribocopyranoside To N-N-dimethylformamide, and add sodium hydride, then add benzyl bromide, react at room temperature to obtain the product. [0004] In references Journal of Organic Chemistry; vol.71; nb.7; (2006); p.2641–2647, Lucero et al. disclose a method for the preparation of 1-methyl-2,3,4-trioxo-benzyl The method of base-β-D-ribopyranoside adopts 1-methyl-β-D-ribopyranoside as raw material, takes sodium hydride and benzyl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/18C07H1/00
Inventor 孟庆文郗遵波宁述光王武宝程经纬李大川顾振磊
Owner 济南尚博医药股份有限公司
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