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Catalytic cracking method for guanosine

A technology of catalytic cracking and guanosine, which is applied in chemical instruments and methods, organic chemistry, esterified saccharides, etc., can solve the problems of unsuitability for large-scale industrial production, low recycling rate, high price of adenine, etc. Large-scale industrial production, low production cost, good product color effect

Active Publication Date: 2010-05-05
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The resin used in this route is expensive, the recycling rate is low, and the price of adenine is also more expensive than guanosine. Overall, the production cost of this route is very high, and it is not suitable for large-scale industrial production.

Method used

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  • Catalytic cracking method for guanosine
  • Catalytic cracking method for guanosine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] The molar ratio of feeding is guanosine: acetic anhydride: trifluoromethanesulfonic acid=1:8:0.001

[0022] In a 250mL three-necked flask equipped with a thermometer and mechanical stirring, add 42.5g of guanosine, 122g of acetic anhydride, and 0.023g of trifluoromethanesulfonic acid, start stirring, heat to 140°C, and keep warm until the end of the reaction (the end point of the reaction is determined by TLC) ), the reaction solution was cooled to 20°C, filtered to obtain the filter cake and filtrate, the filter cake was washed with an appropriate amount of ethyl acetate and dried to obtain off-white solid powder N 2 , 9-diacetylguanine 32.4g, yield 91.7% (calculated as guanosine, the same below.), the purity after detection is 99.7% (high performance liquid chromatography area normalization method, referred to as HPLC, the same below.); The filtrate was evaporated under reduced pressure to remove acetic acid and acetic anhydride to obtain a syrupy substance. After coo...

Embodiment 2

[0024] The catalyst was changed to trifluoromethanesulfonic anhydride, and the molar ratio of feed was guanosine: acetic anhydride: trifluoromethanesulfonic anhydride = 1: 8: 0.001. Other conditions and preparation steps were the same as in Example 1. Get N 2 , 9-diacetylguanine white powder 32.3g, yield 91.4%, after testing purity is 99.7% (HPLC); Obtain 1,2,3,4-O-tetraacetyl-β-D-ribofuranose white solid 40.5g, 86.0% yield, 99.5% purity (HPLC), melting point 82°C-83°C.

Embodiment 3

[0026] The catalyst was changed to trifluoroacetic acid, and the molar ratio of feed was guanosine: acetic anhydride: trifluoroacetic acid = 1: 8: 0.001. Other conditions and preparation steps were the same as in Example 1. Get N 2 , 9-diacetylguanine white powder 31.4g, yield 89.09%, after testing the purity is 99.7% (HPLC); 1,2,3,4-O-tetraacetyl-β-D-ribofuranose white solid 39.5g, 83.9% yield, 99.5% purity (HPLC), melting point 82°C-83°C.

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Abstract

The invention relates to a catalytic cracking method for guanosine which is shown in the formula (I). The catalytic cracking method for guanosine comprises the following steps: the guanosine which is shown in the formula (I) and acetic anhydride react at 50-140 DEG C under the action of catalyst, and the reaction process is tracked; after the reaction finishes, the reaction solution is filtered to obtain filtrated cake A and filtrate A, and the filtrated cake A is washed and dried to obtain N2, 9-diacetylguanine showed in the formula (III); the filtrate A is postprocessed to obtain crude 1, 2, 3, 5-O-tetraacetyl-Beta-D-ribofuranose, and then the crude 1, 2, 3, 5-O-tetraacetyl-Beta-D-ribofuranose is recrystallized with recrystallizing solvent to obtain 1, 2, 3, 5-O-tetraacetyl-Beta-D-ribofuranose crystal. The catalytic cracking method for guanosine uses less catalyst which is cheap and easy to obtain, is convenient for operation, needs low temperature for reaction, ensures that the product has good color, excellent quality, high yield, less impurities and low production cost and is suitable for large-scale industrial production, thereby having obvious implementation value and social and economic benefits.

Description

(1) Field of invention [0001] The invention relates to a method for preparing 1,2,3,5-O-tetraacetyl-β-D-ribofuranose or N 2 , 9-diacetylguanine method. (2) Background technology [0002] 1,2,3,5-O-tetraacetyl-β-D-ribofuranose (referred to as tetraacetyl ribose) is an important pharmaceutical intermediate, which can be used to synthesize broad-spectrum antiviral drug ribavirin, a novel Antineoplastic drug 5-fluorouracil, anti-AIDS drug stavudine, etc. N 2 9-Diacetylguanine (diacetylguanine for short) is an important nucleoside drug intermediate, and its direct alkylation or glycosylation reaction is the synthesis of acyclovir, ganciclovir It is an important way for drugs such as Wei, and these drugs have good anti-herpes and varicella virus effects, so there is a large demand for diacetyl guanine on the market. [0003] Before the present invention was made, Beranek et al published Acetylation and cleavage of perinea nucleus sides, synthesis of 6-azauri-Dine, 5-flurouridi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H13/06C07H1/00C07D473/18
Inventor 李永曙梅丽琴谭成侠颜贻意
Owner ZHEJIANG UNIV OF TECH