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Method of synthesizing 2-deoxy-5-iodo-beta-uridine

A synthesis method and uridine technology, applied in chemical instruments and methods, preparation of sugar derivatives, sugar derivatives, etc., can solve the problems of methods without deprotection and recrystallization, large amount of raw materials, complicated processes, etc. The effect of high yield, low price and low dosage

Inactive Publication Date: 2007-10-17
SHANGHAI DESANO PHARMA INVESTMENT +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The previous reaction route used a large amount of raw materials, high toxicity, complicated process, difficult to control, and no method of deprotection and recrystallization

Method used

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Examples

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Effect test

example 1

[0010] Example 1: 0.96 grams of deoxyribose, 20 milliliters of methanol, 0.08 milliliters of hydrochloric acid, stirred at room temperature for 1 hour, dried by rotary evaporation to remove water, added 5 milliliters of pyridine, 2.1 milliliters of p-chlorobenzoyl chloride, kept at 40 ° C for 2 hours, added 20 milliliters Diisopropyl ether, washed with water, kept at 0-20 °C for about 1 hour to pass hydrogen chloride gas, to obtain 2.38 g of β-chlorosugar, yield 77%, melting point 114.5-116.5 °C. Add 0.58 g of uracil and 0.005 g of ammonium sulfate into 3.3 ml of hexamethyldisilazane, react at 120° C. for 4 hours, and add 45 ml of chloroform to dilute. 2 g of chlorosugar dissolved in 45 ml of chloroform was added dropwise, reacted at 40° C. for 2 hours, and then washed with water to remove impurities. The solvent was spin-dried to give a large amount of solid. The solid was reacted in 100 ml of methanolic ammonia solution for 15 hours, spin-dried and then recrystallized with ...

example 2

[0011] Example 2: 0.96 grams of deoxyribose, 20 milliliters of methanol, 0.08 milliliters of hydrochloric acid, stirred at room temperature for 1 hour, spin-dried to remove water, added 5 milliliters of pyridine, 2.1 milliliters of p-chlorobenzoyl chloride, kept at 40°C for 2 hours, added 20 milliliters of Propyl ether, washed with water, kept at 0-10°C for about 1 hour to pass through anhydrous hydrogen chloride to obtain 2.50 g of β-chlorosugar, yield 80%, melting point 114.5-116.5°C. Add 0.29 g of uracil and 0.005 g of ammonium sulfate into 1.6 ml of hexamethyldisilazane, react at 120° C. for 2 hours, and add 25 ml of chloroform to dilute. 1 g of chlorosugar dissolved in 25 ml of chloroform was added dropwise, reacted at 40°C for 0.5 hour, and then washed with water to remove impurities. The solvent was spin-dried to obtain a large amount of solid. The solid was dissolved in 50 ml of methanolic ammonia solution, reacted for 15 hours, spin-dried and recrystallized with acet...

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PUM

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Abstract

The invention relates to pharmaceutical chemistry technology field. The present invention discloses a synthesis method of 2-deoxy-5-iodo-beta-urdine synthesis method. The method is: heating ura with hexamethyldisilane, reacting with chloro-sugar, removing protecting group in methanol ammonia solution, obtaining 2-deoxy-beta- urdine, reacting with iodine in the presence of silver sulfate to obtain the 2-deoxy-5-iodo-beta-urdine. Compared with the other method, the inventive method has the following character: reaction condition is simple, material is easy to get and toxicity is little, dosage is little. The product yield and purity are high, cost of material reduce 50% more than original method so the present method is suitable for industrial production.

Description

Technical field: [0001] The invention belongs to the field of pharmaceutical chemistry and pharmacy. It specifically relates to a synthesis method of 2-deoxy-5-iodo-β-uridine. Background technique: [0002] 2-Deoxy-5-iodo-β-uridine is a widely used nucleoside, which is of great value in the pharmaceutical field, especially in the synthesis of anti-tumor and anti-AIDS drugs, and its demand is increasing day by day. The previous reaction route used a large amount of raw materials, high toxicity, complicated process, difficult to control, and no deprotection method and recrystallization method. For example: iodination with iodine chloride, iodine chloride is highly toxic. Invention content: [0003] The technical problem to be solved by the present invention is to overcome the shortcomings of the above-mentioned methods, and design a method that can reduce the amount of raw materials and reaction toxicity, and reduce the cost. [0004] The present invention provides a kind...

Claims

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Application Information

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IPC IPC(8): C07H19/073C07H1/00
CPCY02P20/55
Inventor 孟继本李金亮黄飞季奇冯岁寒
Owner SHANGHAI DESANO PHARMA INVESTMENT
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