Method for preparing 2-chloro-4-nitrophenyl-alpha-L-fucoside

A technology of fucosides and nitrobenzene, which is applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., can solve the problems of low yield, unacceptable cost, and expensive starting materials. The effect of simple treatment and low price

Inactive Publication Date: 2013-04-24
BEIJING LEADMAN BIOCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the starting material used in this route is expensive, and the protective group used is not cheap, and the yield is very low, which is unacceptable in cost

Method used

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  • Method for preparing 2-chloro-4-nitrophenyl-alpha-L-fucoside

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: Synthesis of 1-bromo-2,3,4-triacetyl-α-L-fucose:

[0023] Add 30ml of acetic anhydride to a 100ml three-necked bottle, turn on the electric stirrer, add 50mg of L-fucose to the three-necked bottle, if it is not fully dissolved, turn on the water bath and heat until the thermometer reads 40°C, slowly add 0.18g perchlorate with a 1ml syringe acid, the reaction liquid immediately becomes clear, and the reading on the thermometer rises. Remove the hot water bath immediately, keep the reading on the thermometer at about 40°C, and the upper and lower points do not exceed 2°C. Slowly add 7.5gL-fucose for about 40 minutes, and cool naturally to At room temperature, add 30ml of 30% hydrogen bromide acetic acid solution into the above-mentioned three-necked flask, continue to stir for 1.5 hours, TLC detects that the reaction is complete, pour it into 70ml of dichloromethane, wash twice with ice water (30ml×2), and then use Wash twice with 5% sodium bicarbonate (50ml×2)...

Embodiment 2

[0025] Example 2: Synthesis of 1-bromo-2,3,4-triacetyl-α-L-fucose:

[0026] Add 30ml of acetic acid to a 100ml three-necked bottle, turn on the electric stirrer, add 50mg of L-fucose to the three-necked bottle, turn on the water bath and heat until the thermometer reads 40°C, slowly add 0.5g of sulfuric acid with a 1ml syringe, and keep the thermometer reading At about 70°C, slowly add 7.5g of L-fucose for about 40 minutes, cool down to room temperature naturally, add 30ml of 30% hydrogen bromide acetic acid solution into the above-mentioned three-neck flask, continue to stir for 1.5 hours, TLC detects that the reaction is complete, pour into 70ml of dichloromethane, washed twice with ice water (30ml×2), then washed twice with 5% sodium bicarbonate (50ml×2), separated the organic phase, dried, and evaporated to dryness to obtain 16.53g of yellow syrup , recrystallized with ethanol to obtain 13.9 g of off-white solid, yield 85.5%.

[0027] LC-MS: [M] (positive ionization) = 35...

Embodiment 3

[0028] Example 3: Synthesis of 1-bromo-2,3,4-triacetyl-α-L-fucose:

[0029] Add 30ml of acetic anhydride to a 100ml three-necked bottle, turn on the electric stirrer, add 50mg of L-fucose to the three-necked bottle, turn on the water bath and heat until the thermometer reads 40°C, slowly add 2.5g of p-toluenesulfonic acid with a 1ml syringe, Remove the hot water bath, keep the thermometer reading at about 40°C, slowly add 7.5g of L-fucose for about 40 minutes, cool down to room temperature naturally, add 30ml of 30% hydrogen bromide propionic acid solution into the above three-necked bottle, continue Stir for 2.0 hours, TLC detects that the reaction is complete, cool to room temperature, pour into 70ml of dichloromethane, wash twice with ice water (30ml×2), then wash twice with 5% sodium bicarbonate (50ml×2), divide The organic phase was taken out, dried, and evaporated to dryness to obtain 14.86 g of yellow syrup, which was recrystallized with ethanol to obtain 12.6 g of off-...

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Abstract

The invention relates to a method for preparing 2-chloro-4-nitrophenyl-alpha-L-fucoside and belongs to the field of medicine production. The method comprises the following steps of: performing hydroxyl protection and bromination on L-fucoside to obtain 1-bromo-2,3,4-triacetyl-alpha-L-fucoside; reacting the 1-bromo-2,3,4-triacetyl-L-fucoside with ethanethiol to obtain ethyl-1-mercapto-2,3,4-triacetyl-beta-L-fucoside; reacting the ethyl-1-mercapto-2,3,4-triacetyl-beta-L-fucoside with 2-chloro-4-nitrophenol to obtain 2-chloro-4-nitrophenyl-2,3,4-triacetyl-alpha-L-fucoside; and removing protection groups from the 2-chloro-4-nitrophenyl-2,3,4-triacetyl-alpha-L-fucoside to obtain the 2-chloro-4-nitrophenyl-alpha-L-fucoside. According to a product obtained by the method, alpha-configuration products are high in proportion; and the method has a good industrial production prospect.

Description

technical field [0001] The invention relates to a method for preparing 2-chloro-4-nitrobenzene-α-L-fucoside. Background technique [0002] 2-Chloro-4-nitrobenzene-α-L-fucoside is an important raw material for diagnostic reagents. At present, this product is widely used in the market, and the unit price is very high. Due to the difficulty in synthesis, the domestic market is mainly based on imports. [0003] The earliest literature to report the synthesis of this compound was a Japanese patent (JP 06-179690) published in 1994. The synthesis method used by the author (Koichi) has been verified by our experiments, and it is found that the route is difficult to repeat and there are more β-isomers in the product. The obtained product cannot be normally used in the company's self-produced kit. In 2004, Du Yuguo and others from the Eco-Environmental Research Center of the Chinese Academy of Sciences reported a synthetic route starting from ethyl-1-mercapto-β-L-fucoside as the s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/203C07H1/00
CPCY02P20/55
Inventor 不公告发明人
Owner BEIJING LEADMAN BIOCHEM
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