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The preparation method of 2-deoxy-l-ribofuranose

A technology of ribofuranose and tetrahydrofuran, which is applied in the field of medicine, can solve the problems of flammable raw materials, long steps, expensive and difficult to obtain raw materials, etc.

Active Publication Date: 2015-11-18
FUJIAN RIBIO TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, the first three methods above are either expensive raw materials, such as the market price of L-ribose is as high as 6000 yuan / Kg; or the steps are too long, the yield is too low, and the production cost is too high, which is unacceptable to the market
In contrast, the most practical is to synthesize 2-deoxy-L-ribofuranose from L-arabinose, but in the reported synthesis of 2-deoxy-L-ribofuranose from L-arabinose In the route, either because the intermediate reactant phenoxythiocarbonyl chloride is expensive and not easy to obtain, or because the use of CS 2 Raw material is flammable
In addition, the follow-up reducing agent also has the problem of expensive and difficult-to-obtain raw materials, which makes the overall production cost higher

Method used

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  • The preparation method of 2-deoxy-l-ribofuranose
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  • The preparation method of 2-deoxy-l-ribofuranose

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Embodiment 1

[0059] (1) Methylation: Put 100g of L-arabinose and 800mL of methanol with a concentration of 95% into the reaction kettle, stir and dissolve, add HCl methanol solution dropwise, the concentration of HCl in it is 0.01mol / l, and react at room temperature for 5 hours. After the reaction is completed, add sodium carbonate to neutralize, filter, and put the solution into the next step after the solution is spin-dried;

[0060] (2) Protection of hydroxyl groups at positions 3 and 5: Put the product from the previous step into the reactor, add 400 mL of tetrahydrofuran, 110 g of benzaldehyde dimethyl acetal and 5 g of p-toluenesulfonic acid as a catalyst, and react at 50°C. After the reaction is completed, the remaining benzaldehyde dimethyl acetal and tetrahydrofuran are removed by distillation, toluene is added and washed with sodium bicarbonate solution to neutrality, the solvent is removed by distillation under reduced pressure, crystallized with methanol, and put into the next s...

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Abstract

The invention provides a preparation method of 2-deoxy-L-ribofuranose. The preparation method comprises the following steps: carrying out 3,5-site hydroxy protection on methylated L-arabinose; carrying out 2-site deoxygenation on the L-arabinose; and carrying out 3,5-site hydroxy deprotection on the obtained product. The preparation method has the advantages of available raw materials, short synthetic route, improved product yield and purity, low production cost and the like, and is simple to operate.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to a preparation method of a pharmaceutical intermediate 2-deoxy-L-ribofuranose. Background technique [0002] As antiviral, anti-AIDS and anti-tumor drugs, L-nucleoside drugs have attracted widespread attention since the 1950s because their toxicity is lower than that of their enantiomers. 2-deoxy-L-ribofuranose, its structural formula is as follows: [0003] [0004] As an important intermediate for the synthesis of L-nucleoside drugs with new biological activity, it has always been a research hotspot for scientists in various fields. [0005] However, 2-deoxy-L-ribofuranose is a kind of unnatural ribose, which can only be synthesized by chemical or biological methods. Synthesis of 2-deoxy-L-ribofuranose; 2) Synthesis of 2-deoxy-L-ribofuranose by reduction of L-ribose; 3) Synthesis of 2-deoxy-L-ribofuranose with ascorbic acid; 4) Synthesis of 2-deoxy-L-ribofuranose with L-...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H3/08C07H1/00
Inventor 陈振昌张红娟
Owner FUJIAN RIBIO TECH CO LTD