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Method for synthesizing 1,2,3-O-triacetyl-5-deoxy-D-ribofuranose by using solid acid SO4<2->/gamma-Al2O3 as catalyst

A technology of ribofuranose and triacetyl, which is applied in the field of solid acid SO42-/γ-AL2O3 catalytic synthesis of 1, 2, 3-O-triacetyl-5-deoxy-D-ribofuranose, which can solve the complex post-processing , a large amount of waste water, environmental pollution and other problems, to achieve the effect of simple post-processing, no corrosion of equipment, and environmental friendliness

Inactive Publication Date: 2012-02-08
JIANGXI SCI & TECH NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] This method is a two-step reaction, with long reaction steps, many side reactions, low yield and product purity, complex post-treatment and a large amount of waste water, causing environmental pollution, serious corrosion of equipment, and high requirements for personnel protection, which is not conducive to large-scale production. Large-scale industrial production

Method used

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  • Method for synthesizing 1,2,3-O-triacetyl-5-deoxy-D-ribofuranose by using solid acid SO4&lt;2-&gt;/gamma-Al2O3 as catalyst
  • Method for synthesizing 1,2,3-O-triacetyl-5-deoxy-D-ribofuranose by using solid acid SO4&lt;2-&gt;/gamma-Al2O3 as catalyst
  • Method for synthesizing 1,2,3-O-triacetyl-5-deoxy-D-ribofuranose by using solid acid SO4&lt;2-&gt;/gamma-Al2O3 as catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Dissolve 5.0 g, 26.6 mmol, of 1-methyl-2,3-O-isopropylidene-5-deoxy-D-ribofuranose in 50 ml of acetic anhydride / acetic acid at an equal volume ratio, and add 0.5 g of solid acid SO 4 2- / γ-Al 2 o 3 , stirred at room temperature for 1 h, raised the temperature to 50° C., continued to react for 2 h, then added 25 ml of water, filtered, and the filtrate was adjusted to pH 7 with saturated sodium bicarbonate. Then extract with 50ml of dichloromethane, separate the layers, wash the organic phase with 50ml of saturated brine, dry over anhydrous sodium sulfate, evaporate the solvent under conventional reduced pressure, and concentrate to dryness to obtain the target product 1,2,3-O-triacetyl 5.8 g of base-5-deoxy-D-ribofuranose, the yield was 85.6%, and the purity by gas chromatography was 95.1%.

Embodiment 2

[0015] By the method of embodiment 1, reaction temperature is changed into 80 ℃, other methods are unchanged. The target product 1, 2, 3-O-triacetyl-5-deoxy-D-ribofuranose was 6.1 g, the yield was 90.0%, and the purity by gas chromatography was 93.6%.

Embodiment 3

[0017] According to the method of Example 1, after stirring at room temperature for 2 hours, the reaction was carried out at 50° C. for 3 hours, and the other methods remained unchanged. The target product 1, 2, 3-O-triacetyl-5-deoxy-D-ribofuranose was 6.3 g, the yield was 93.0%, and the gas chromatography purity was 96.8%.

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Abstract

The invention relates to a method for synthesizing 1,2,3-O-triacetyl-5-deoxy-D-ribofuranose by using solid acid SO4<2-> / gamma-Al2O3 as a catalyst, which comprises the following steps of: dissolving 1-methyl-2,3-O-isopropylidene-5-deoxy-D-ribofuranose in isometric acetic anhydride / acetic acid, and adding solid acid SO4<2-> / gamma-Al2O3; stirring at room temperature, heating, and continuing the reaction; and regulating the pH value to neutral with an alkaline matter, carrying out liquid dispensation, washing with water, drying, and carrying out conventional reduced pressure distillation to remove the solvent, thereby obtaining the target product. By using the solid acid SO4<2-> / gamma-Al2O3 as the catalyst, the invention overcomes the defects of liquid acid, can activate the acid catalyzed reaction under mild conditions, and has the characteristics of high selectivity, fewer side reactions, easiness in separation from the liquid phase reaction system, no equipment corrosion, simple after-treatment, environment friendliness and the like.

Description

technical field [0001] The present invention relates to a kind of solid acid SO 4 2- / γ-Al 2 o 3 A method for the catalytic synthesis of 1,2,3-O-triacetyl-5-deoxy-D-ribofuranose. Background technique [0002] Capecitabine (capecitabine), the chemical name is 5'-deoxy-5-fluoro-N-[(pentyloxy)carbonyl] cytidine, developed by Swiss Hoffmann-La Roche company, first listed in Switzerland in 1998, is A new oral flucytosine nucleoside analog, which is mainly used clinically for the treatment of advanced breast cancer, colorectal cancer and other solid tumors. 1, 2, 3-O-triacetyl-5-deoxy-D-ribofuranose is an essential intermediate for the synthesis of anti-tumor drug capecitabine, and it is also suitable for the synthesis of various 5'-deoxynucleosides compound. Its structure is as follows: [0003] [0004] Synthesis of 1, 2, 3-O-triacetyl-5-deoxy-D-ribofuranose from 1-methyl-2,3-O-isopropylidene-5-deoxy-D-ribofuranose reported in literature Most of the methods are to...

Claims

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Application Information

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IPC IPC(8): C07H13/06C07H1/00
Inventor 王晓季刘东旺
Owner JIANGXI SCI & TECH NORMAL UNIV
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