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Synthesis method of cordycepin

A synthesis method and a technology for cordycepin, which are applied in chemical instruments and methods, preparation of sugar derivatives, sugar derivatives, etc., can solve the problems of expensive raw materials, increased manufacturing costs, etc., and achieve high yield, simple operation and little waste. Effect

Inactive Publication Date: 2018-11-23
SHANDONG BENYUE BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the raw materials selected in the synthetic methods in the prior art are expensive, which increases the manufacturing cost. At the same time, because the selected raw materials have certain toxicity, they cause huge pressure on the safety of production operations and environmental protection. Comprehensive analysis of the current synthetic approach cannot To better meet the needs of the current consumer market, more green and healthy synthetic approaches and methods are needed to improve the shortcomings in the current production and processing process and meet people's growing pursuit of high-quality and healthy life

Method used

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  • Synthesis method of cordycepin
  • Synthesis method of cordycepin
  • Synthesis method of cordycepin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Put 2.35g of 9-β-D-ribofuranosyl adenine, 2g of triethyl orthoformate, and 12ml of anhydrous acetic acid into a 50ml reaction bottle, keep the reaction at 50°C for 3 hours, reduce the pressure to -0.08MPa, and concentrate to dryness. Get caramel A3.0g;

[0034] Dissolve 3.0 g of the caramel A obtained in the previous step in 17 ml of dichloromethane, add 6.5 g of acetyl bromide dropwise at 0°C, and react at room temperature for 5 hours. Slowly add 10ml of water dropwise at room temperature, after the drop is complete, stir at room temperature for 10 minutes, adjust the pH value to 8 with saturated sodium bicarbonate, separate the organic layer, and pass through a silica gel column with a mass ratio of dichloromethane:methanol=9:1 as the eluent Purified by chromatography to obtain caramel B1.9g;

[0035] Add 20ml of triethylsilane and 10ml of trifluoroacetic acid to 1.9g of the obtained caramel B, heat to reflux for 12 hours, reduce the pressure to -0.08MPa, and concent...

Embodiment 2

[0037] Put 2g of 9-β-D-ribofuranosyl adenine, 1.71g of triethyl orthoformate, and 10ml of anhydrous acetic acid into a 50ml reaction bottle, keep the reaction at 50°C for 4 hours, reduce the pressure to -0.08MPa, and concentrate to dryness to obtain Caramel A2.6g;

[0038] Dissolve 2.6 g of caramel A obtained in the previous step in 16 ml of dichloromethane, add 6 g of acetyl bromide dropwise at 0°C, and react at room temperature for 5 hours after the drop is complete. Slowly add 10ml of water dropwise at room temperature, after the drop is complete, stir at room temperature for 10 minutes, adjust the pH value to 8 with saturated sodium bicarbonate, separate the organic layer, and pass through a silica gel column with a mass ratio of dichloromethane:methanol=9:1 as the eluent Purified by chromatography to obtain caramel B1.6g;

[0039] Add 21ml of triethylsilane and 8ml of trifluoroacetic acid to 1.6g of the obtained caramel B in the upward step, heat and reflux for 12 hours,...

Embodiment 3

[0041] Put 3.1g of 9-β-D-ribofuranosyl adenine, 2.5g of triethyl orthoformate, and 15ml of anhydrous acetic acid into a 50ml reaction bottle, keep the reaction at 50°C for 2 hours, reduce the pressure to -0.08MPa, and concentrate to dryness. Get caramel A3.4g;

[0042] Dissolve 3.4g of the caramel A obtained in the previous step in 18ml of dichloromethane, add 5.9g of acetyl bromide dropwise at 0°C, and react at room temperature for 6 hours. Slowly add 13ml of water dropwise at room temperature, after dropping, stir at room temperature for 10 minutes , the pH value was adjusted to 8 with saturated sodium bicarbonate, the organic layer was separated, and the mass ratio of dichloromethane:methanol=9:1 was used as the eluent to purify by silica gel column chromatography to obtain caramel B2.7g;

[0043] Add 25ml of triethylsilane and 12ml of trifluoroacetic acid to 2.7g of the obtained caramel B, heat to reflux for 12 hours, reduce the pressure to -0.08MPa, and concentrate to dry...

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Abstract

The invention relates to a synthesis method of cordycepin and belongs to the technical field of cordyceps health products. The synthesis method comprises the following steps: adding adenosine, triethyl orthoformate and glacial acetic acid into a reaction flask, carrying out pressure-reduced concentration until the concentrated product is dry to obtain a caramel-like product A; dissolving the obtained caramel-like product A in dichloromethane, dropwise adding acetyl bromide at 0 DEG C, reacting for 4-6 hours under room temperature, continuously dropwise adding water after the reaction is ended,stirring for 10 minutes under room temperature, adjusting the pH value to 8 by using saturated sodium bicarbonate, and separating an organic layer to obtain a caramel-like product B; adding triethylsilicane and trifluoroacetic acid into the obtained caramel-like product B, heating and refluxing for 12 hours, carrying out pressure-reduced concentration until the concentrated product is dry, adding a saturated methanol ammonia solution, reacting under room temperature, carrying out pressure-reduced concentration until the concentrated product is dry, recrystallizing residues by using alcohol to obtain white solid which is cordycepin. The synthesis method has the advantages of high yield, low cost, low waste and simplicity and convenience in operation.

Description

technical field [0001] The invention relates to a synthesis method of cordycepin, which belongs to the technical field of cordyceps health products. Background technique [0002] Cordycepin, also known as cordycepin and cordycepin, is the main active ingredient in Cordyceps militaris and the first nucleoside antibiotic isolated from fungi. Cordycepin is a drug of natural origin, which has various pharmacological effects such as antitumor, antibacterial and antiviral, immune regulation, and scavenging free radicals, and has a good clinical application prospect. Cordycepin research is now becoming an extremely active field in medicinal chemistry. The content of cordycepin in wild Cordyceps sinensis is very small, and the cordycepin used in current research is generally extracted from fermented Cordyceps militaris. Cordycepin has the following effects: 1. The effect of inhibiting bacteria: Cordycepin can inhibit Mycobacterium avium Chester; 43 strains are inhibited in 45 stra...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/16C07H1/00
CPCC07H1/00C07H19/16
Inventor 马志强陈良王振东
Owner SHANDONG BENYUE BIOTECH
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