CN111484535A - Method for preparing 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1- β -D-ribofuranose - Google Patents
Method for preparing 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1- β -D-ribofuranose Download PDFInfo
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Abstract
The invention relates to the field of organic synthesis, in particular to a method for preparing 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1- β -D-ribofuranose, which comprises the following steps of mixing D-ribose with methanol and a catalyst, heating for reaction, neutralizing, concentrating to obtain a methyl esterification intermediate III, mixing the methyl esterification intermediate III with an organic solvent, 4-dimethylaminopyridine and an acid agent, cooling, dropwise adding benzoyl chloride for reaction, washing with water for layering, drying to obtain a benzoylation intermediate II, mixing the benzoylation intermediate II with the organic solvent and acetic anhydride, adding the catalyst, stirring, keeping the temperature at 0-70 ℃ for 10-20 hours for reaction, cooling for crystallization after the reaction is qualified, centrifuging to obtain a crude product, finally recrystallizing, centrifuging and drying to obtain the 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1- β -D-ribofuranose, and has the advantages of short reaction steps, high chemical and optical purity, easiness in operation, low cost, environmental friendliness, suitability for industrial production and the like.
Description
Technical Field
The invention relates to the field of organic synthesis, in particular to a method for preparing 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1- β -D-ribofuranose.
Background
The product has wide application, for example, (1) the cromolbine is a novel purine nucleoside anticancer drug, the national praise company (Genzyme Corporation, NASDAQ: GENZ) with the first ten biological pharmaceutical companies is successfully developed, the product is under the name of clofarine, the Food and Drug Administration (FDA) in 28 Japanese 2004 approved by a fast channel for the treatment of intractable or recurrent acute lymphoblastic leukemia of children, the product is the only drug which can be specifically used for the treatment of the acute lymphoblastic leukemia of children (A LL) at present, has high efficiency for the treatment of the leukemia, has good tolerability, can not be administrated predictably, can be used for the treatment of intravenous leukemia, and also can be used for the treatment of the acute lymphoblastic leukemia of children (A LL), and has the best effect on the treatment of the acute lymphoblastic leukemia of the children, the most effective medicaments of the cervical cancer, the anti-metabolism of the HIV, the anti-tumor virus and the like, and has the best effect on the treatment of the acute lymphoblastic leukemia of the cervical cancer.
1-O-acetyl-2, 3, 5-tri-O-benzoyl-1- β -D-ribofuranose has attracted much interest and attention worldwide, and related research articles are still published, so that the method for preparing 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1- β -D-ribofuranose reported in the current literature mostly uses pyridine as a solvent, has the disadvantages of long reaction steps, great environmental pollution, high cost and the like, for example, the conventional Junbiao (publication No. CN101177442A) synthesizes the product by using pyridine as a solvent through four-step reaction starting from D-ribose, uses dangerous products such as bromine, red phosphorus and the like, and further needs column separation, meanwhile, racemic pure products are not synthesized, and are reacted as intermediate products, wherein plum et al (application No. CN108570078) starts from adenosine and synthesizes the product by two-step method, but has few steps, but raw materials, Baud (Tetrahedron L, 1990.4431.31, 4431.31-4431.31.31.31.31.31.31.4431 to 99.31.31.31.31.31.31.31.31.vol% of pyridine, and the method is synthesized by three-step, and the method, and the purity of pyridine is not reached by three-step reaction, and the same method, and.
Disclosure of Invention
The present invention is directed to a method for preparing 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1- β -D-ribofuranose, which solves the problems of the prior art.
In order to achieve the above objects, the present invention provides a method for preparing 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1- β -D-ribofuranose, comprising the steps of:
s1: methyl esterification reaction: mixing D-ribose with methanol and a catalyst, heating to 30-70 ℃ for reaction for 6-24 hours, neutralizing after qualified detection, and concentrating to obtain a methyl esterification intermediate III;
s2: benzoylation reaction: mixing the methyl esterification intermediate III with an organic solvent and an acid-binding agent, adding 4-dimethylaminopyridine as a catalyst, cooling, dropwise adding benzoyl chloride for reaction, washing with water, drying with anhydrous sodium sulfate, filtering and concentrating to obtain a benzoylation intermediate II;
and S3, performing acetylation, namely mixing the benzoylation intermediate II with an organic solvent and acetic anhydride, adding a catalyst, stirring, performing heat preservation reaction at the temperature of 0-70 ℃ for 10-20 hours, cooling, crystallizing and centrifuging after the reaction is qualified to obtain a crude product, recrystallizing with the organic solvent, and centrifuging and drying to obtain the 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1- β -D-ribofuranose.
Preferably, in the S1) methyl esterification reaction, the molar ratio of the D-ribose to the catalyst to the methanol is 1 to (0.001-0.1) to (10-50); wherein the catalyst is concentrated sulfuric acid, p-toluenesulfonic acid, methanesulfonic acid, hydrobromic acid, hydrochloric acid or HCl gas.
Preferably, in the S1) methyl esterification reaction, the molar ratio of the D-ribose to the catalyst to the methanol is 1 to (0.005-0.02) to (20-30); wherein the catalyst is concentrated sulfuric acid or p-toluenesulfonic acid.
Preferably, in the S2) benzoylation reaction, the molar ratio of benzoyl chloride to acid-binding agent and D-ribose is (3-7) to (4-9) to 1, wherein the organic solvent is chloroform, 1, 2-dichloroethane, dichloromethane, ethyl acetate, N-dimethylformamide, triethylamine or toluene; wherein the acid-binding agent is triethylamine, methyl diisopropylamine, potassium carbonate, sodium bicarbonate or cesium carbonate.
Preferably, in the step S2) of benzoylation, the molar ratio of benzoyl chloride to acid-binding agent and D-ribose is as follows: (3-5) to (4-7) to 1; wherein the organic solvent is toluene, trichloromethane or 1, 2-dichloroethane; wherein the acid-binding agent is triethylamine and methyl diisopropylamine
Preferably, in the acetylation reaction of S3), the molar ratio of acetic anhydride to the catalyst and D-ribose is: (1-5) to (0.001-0.5) to 1, wherein the catalyst is concentrated sulfuric acid, p-toluenesulfonic acid, methanesulfonic acid or HCl gas; wherein the organic solvent is acetic acid, toluene, ethyl acetate, dichloromethane, trichloromethane, 1, 2-dichloroethane; wherein the crystallization solvent is ethyl acetate, methanol, ethanol, isopropanol, toluene, dichloromethane, chloroform, 1, 2-dichloroethane, etc.
Preferably, in the acetylation reaction of S3), the molar ratio of acetic anhydride to the catalyst and D-ribose is: 1-2: 0.1-0.2: 1; wherein the catalyst is concentrated sulfuric acid and p-toluenesulfonic acid; wherein the organic solvent is acetic acid, toluene, dichloromethane, trichloromethane, 1, 2-dichloroethane; wherein the crystallization solvent is one or a mixture of two or more of toluene, ethanol, isopropanol, dichloromethane and chloroform.
Compared with the prior art, the method for preparing the 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1- β -D-ribofuranose has the advantages of short reaction steps, high chemical and optical purity, simplicity in operation, easiness in obtaining raw materials, low cost, small amount of three wastes, environmental friendliness and the like, and is suitable for industrial production.
Drawings
FIG. 1 is a schematic diagram of the chemical reaction process of the present invention.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Referring to FIG. 1, the present invention provides a method for preparing 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1- β -D-ribofuranose, comprising the steps of:
s1: methyl esterification reaction: mixing D-ribose with methanol and a catalyst, heating to 30-70 ℃ for reaction for 6-24 hours, neutralizing after qualified detection, and concentrating to obtain a methyl esterification intermediate III;
s2: benzoylation reaction: mixing the methyl esterification intermediate III with an organic solvent and an acid-binding agent, adding 4-dimethylaminopyridine as a catalyst, cooling, dropwise adding benzoyl chloride for reaction, washing with water, drying with anhydrous sodium sulfate, filtering and concentrating to obtain a benzoylation intermediate II;
and S3, performing acetylation, namely mixing the benzoylation intermediate II with an organic solvent and acetic anhydride, adding a catalyst, stirring, performing heat preservation reaction at the temperature of 0-70 ℃ for 10-20 hours, cooling, crystallizing and centrifuging after the reaction is qualified to obtain a crude product, recrystallizing with the organic solvent, and centrifuging and drying to obtain the 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1- β -D-ribofuranose.
Furthermore, in the S1) methyl esterification reaction, the molar ratio of the D-ribose to the catalyst to the methanol is 1 to (0.001-0.1) to (10-50); wherein the catalyst is concentrated sulfuric acid, p-toluenesulfonic acid, methanesulfonic acid, hydrobromic acid, hydrochloric acid or HCl gas.
Furthermore, in the S1) methyl esterification reaction, the molar ratio of the D-ribose to the catalyst to the methanol is 1 to (0.005-0.02) to (20-30); wherein the catalyst is concentrated sulfuric acid or p-toluenesulfonic acid.
Further, in the S2) benzoylation reaction, the molar ratio of benzoyl chloride to acid binding agent and D-ribose is as follows: (3-7) to (4-9) to 1, wherein the organic solvent is chloroform, 1, 2-dichloroethane, dichloromethane, ethyl acetate, N-dimethylformamide, triethylamine or toluene; wherein the acid-binding agent is triethylamine, methyl diisopropylamine, potassium carbonate, sodium bicarbonate or cesium carbonate.
Further, in the benzoylation reaction of S2), the molar ratio of benzoyl chloride to acid binding agent and D-ribose is (3-5) to (4-7) to 1; wherein the organic solvent is toluene, trichloromethane or 1, 2-dichloroethane; wherein the acid-binding agent is triethylamine and methyl diisopropylamine
Further, in the acetylation reaction of S3), the molar ratio of acetic anhydride to the catalyst to the D-ribose is: (1-5) to (0.001-0.5) to 1, wherein the catalyst is concentrated sulfuric acid, p-toluenesulfonic acid, methanesulfonic acid or HCl gas; wherein the organic solvent is acetic acid, toluene, ethyl acetate, dichloromethane, trichloromethane, 1, 2-dichloroethane; wherein the crystallization solvent is ethyl acetate, methanol, ethanol, isopropanol, toluene, dichloromethane, chloroform, 1, 2-dichloroethane, etc.
Further, in the acetylation reaction of S3), the molar ratio of acetic anhydride to the catalyst to the D-ribose is: 1-2: 0.1-0.2: 1; wherein the catalyst is concentrated sulfuric acid and p-toluenesulfonic acid; wherein the organic solvent is acetic acid, toluene, dichloromethane, trichloromethane, 1, 2-dichloroethane; wherein the crystallization solvent is one or a mixture of two or more of toluene, ethanol, isopropanol, dichloromethane and chloroform.
Example 1:
methyl esterification reaction: putting 0.09g of TsOH and 85.0g of methanol into a 250ml three-necked bottle (stirring and condensing tube), adding 15.0g D-ribose, reacting at 30-50 ℃ to be qualified, adding triethylamine to quench the reaction, and concentrating to obtain a methyl esterification intermediate III which is directly used for the next reaction;
benzoylation, namely adding a methyl esterification intermediate III, 80.0m L1, 2-dichloroethane and 72m L triethylamine into a 500m L three-necked flask provided with a mechanical stirrer and a thermometer, stirring, then adding 0.15g of DMAP, stirring and dissolving, dropwise adding 20m L1, 2-dichloroethane and 63.0g of benzoyl chloride at the temperature of 30 ℃, completely reacting at the temperature of 30 ℃, and performing aftertreatment and filtration to obtain a benzoylation intermediate II which is directly used for the next reaction;
acetylation, mixing the benzoylated intermediate II with 80ml ethyl acetate and 25g acetic anhydride, adding 6.0g sulfuric acid, stirring at 50-60 deg.C, filtering to obtain crude product 45.07g, recrystallizing and oven drying to obtain white solid 30.0g 1-O-acetyl-2, 3, 5-tri-0-benzoyl-1- β -D-ribofuranose.
The obtained 1-0-acetyl-2, 3, 5-tri-0-benzoyl-1- β -D-ribofuranose had a total yield of 59.45%, a HP L C purity of 99.43%, a melting point of 129.2 to 130.4 ℃, and a specific rotation [ α ]20D ═ 24.3 ° (C ═ 1, pyridine).
Example 2:
methyl esterification reaction: putting 0.09g of TsOH and 85.0g of methanol into a 250ml three-necked bottle (stirring and condensing tube), adding 15.0g D-ribose, reacting at normal temperature, adding triethylamine, quenching, and concentrating to obtain a methyl esterification intermediate III which is directly used for the next reaction;
benzoylation, namely adding a methyl esterification intermediate III, 80.0m L dichloromethane and 75m L triethylamine into a 500m L three-necked bottle provided with a mechanical stirrer and a thermometer, then adding 0.15g DMAP (dimethyl formamide), stirring and dissolving, dropwise adding 20ml dichloromethane and 60.50g benzoyl chloride at 40-50 ℃, reacting at 50 ℃ after dropwise adding, and filtering to obtain a benzoylation intermediate II which is directly used for the next reaction;
and (3) acetylation, namely adding the benzoylation intermediate II, 80m of acetic acid L and 25.0g of acetic anhydride into a 500ml reaction bottle, adding 2g of sulfuric acid, stirring at normal temperature, concentrating to obtain 48.0g of crude product after the reaction is qualified, recrystallizing, filtering and drying to obtain 33.1g of 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1- β -D-ribofuranose as a white solid.
The obtained 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1- β -D-ribofuranose had a total yield of 65.61%, a HP L C purity of 99.55%, a melting point of 129.6 to 130.8 ℃, and a specific rotation [ α ]20D ═ 24.2 ° (C ═ 1, pyridine).
Example 3:
methyl esterification, namely putting 10g of concentrated sulfuric acid and 8500g of methanol into a 20L reaction kettle (stirring and condensing tube), adding 1500g D-ribose, heating to 50 ℃ for reaction, adding triethylamine after the reaction is qualified, quenching the reaction, and concentrating to obtain a methyl esterification intermediate III which is directly used for the next reaction;
benzoylation, namely adding a methyl esterification intermediate III, 8L trichloromethane and 8.2L triethylamine into a 50L reaction kettle provided with a mechanical stirrer and a thermometer, adding 15g DMAP, stirring and dissolving, dropwise adding 2L trichloromethane and 6790g benzoyl chloride at 30-40 ℃, reacting for 2 hours at 50 ℃ after dropwise adding, and completely reacting;
acetylation, namely mixing the benzoylation intermediate II obtained in the previous step with 8L acetic acid solution in a 20L reaction kettle, adding 1230g of acetic anhydride, adding 60g of sulfuric acid, stirring at 50 ℃ to be qualified, centrifuging to obtain 4732g of crude product, recrystallizing, filtering and drying to obtain 3122g of white solid 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1- β -D-ribofuranose.
The obtained 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1- β -D-ribofuranose had a total yield of 61.85%, a purity of 99.32% for HP L C, a melting point of 129.1 to 130.3 ℃, and a specific rotation [ α ]20D ═ 24.4 ° (C ═ 1, pyridine).
Example 4:
methyl esterification, namely putting 45g of TsOH and 42.5Kg of methanol into a 100L reaction kettle (stirring and condensing tube), adding 7.5Kg of D-ribose, heating to 60 ℃ for reaction, adding methyl diisopropylamine, quenching, reacting and concentrating to obtain a methyl esterification intermediate III, and directly using the methyl esterification intermediate III in the next reaction;
benzoylation, namely adding a methyl esterification intermediate III, 40L toluene and 41.3L methyl diisopropylamine into a 200L reaction kettle provided with a mechanical stirrer and a thermometer, adding 75g of DMAP, stirring until the methyl esterification intermediate III, the 40L toluene and the 41.3L methyl diisopropylamine are completely dissolved, dropwise adding 10L toluene and 36.38kg of benzoyl chloride at 40 ℃, reacting at 50 ℃, filtering to obtain a benzoylation intermediate II, and directly using the benzoylation intermediate II in the next reaction;
acetylation, namely mixing the benzoylation intermediate II obtained in the previous step with 40L acetic acid in a 200L reaction kettle, adding 6.2Kg of acetic anhydride, adding 300g of sulfuric acid, stirring at 50 ℃, centrifuging to obtain 23.5Kg of crude product after passing the detection, recrystallizing, filtering and drying to obtain 16.3Kg of white solid 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1- β -D-ribofuranose.
The obtained 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1- β -D-ribofuranose had a total yield of 64.62%, a HP L C purity of 99.49%, a melting point of 129.4 to 130.7 ℃, and a specific rotation [ α ]20D ═ 24.0 ° (C ═ 1, pyridine).
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (7)
1. A method for preparing 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1- β -D-ribofuranose, which is characterized by comprising the following steps:
s1: methyl esterification reaction: mixing D-ribose with methanol and a catalyst, heating to 30-70 ℃ for reaction for 6-24 hours, neutralizing after qualified detection, and concentrating to obtain a methyl esterification intermediate III;
s2: benzoylation reaction: mixing the methyl esterification intermediate III with an organic solvent and an acid-binding agent, adding 4-dimethylaminopyridine as a catalyst, cooling, dropwise adding benzoyl chloride for reaction, washing with water, drying with anhydrous sodium sulfate, filtering and concentrating to obtain a benzoylation intermediate II;
and S3, performing acetylation, namely mixing the benzoylation intermediate II with an organic solvent and acetic anhydride, adding a catalyst, stirring, performing heat preservation reaction at the temperature of 0-70 ℃ for 10-20 hours, cooling, crystallizing and centrifuging after the reaction is qualified to obtain a crude product, recrystallizing with the organic solvent, and centrifuging and drying to obtain the 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1- β -D-ribofuranose.
2. The method of claim 1, wherein the molar ratio of D-ribose to the catalyst and methanol in the S1) methyl esterification reaction is 1: 0.001-0.1: 10-50, and the catalyst is concentrated sulfuric acid, p-toluenesulfonic acid, methanesulfonic acid, hydrobromic acid, hydrochloric acid or HCl gas.
3. The method for preparing 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1- β -D-ribofuranose according to claim 2, wherein the molar ratio of D-ribose to catalyst and methanol in the S1) methyl esterification reaction is 1: 0.005-0.02: 20-30, and the catalyst is concentrated sulfuric acid or p-toluenesulfonic acid.
4. The method for preparing 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1- β -D-ribofuranose according to claim 1, wherein the mole ratio of benzoyl chloride to acid-binding agent and D-ribose in the benzoylation reaction of S2 is (3-7): (4-9): 1, wherein the organic solvent is chloroform, 1, 2-dichloroethane, dichloromethane, ethyl acetate, N-dimethylformamide, triethylamine or toluene, and wherein the acid-binding agent is triethylamine, methyl diisopropylamine, potassium carbonate, sodium bicarbonate or cesium carbonate.
5. The method for preparing 1-O-acetyl-2, 3, 5-tri-0-benzoyl-1- β -D-ribofuranose according to claim 4, wherein the molar ratio of benzoyl chloride to acid-binding agent and D-ribose in the benzoylation reaction of S2 is (3-5) to (4-7) to 1, wherein the organic solvent is toluene, chloroform or 1, 2-dichloroethane, and wherein the acid-binding agent is triethylamine or methyl diisopropylamine.
6. The method for preparing 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1- β -D-ribofuranose according to claim 1, wherein the molar ratio of acetic anhydride to catalyst and D-ribose in the acetylation reaction of S3) is (1-5): (0.001-0.5): 1, wherein the catalyst is concentrated sulfuric acid, p-toluenesulfonic acid, methanesulfonic acid or HCl gas, wherein the organic solvent is acetic acid, toluene, ethyl acetate, dichloromethane, trichloromethane, 1, 2-dichloroethane, and wherein the crystallization solvent is ethyl acetate, methanol, ethanol, isopropanol, toluene, dichloromethane, trichloromethane, 1, 2-dichloroethane.
7. The method for preparing 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1- β -D-ribofuranose according to claim 6, wherein the molar ratio of acetic anhydride to the catalyst to D-ribose in the acetylation reaction of S3 is (1-2) to (0.1-0.2) to 1, wherein the catalyst is concentrated sulfuric acid and p-toluenesulfonic acid, wherein the organic solvent is one or a mixture of two or more of acetic acid, toluene, dichloromethane, trichloromethane and 1, 2-dichloroethane, and wherein the crystallization solvent is one or a mixture of two or more of toluene, ethanol, isopropanol, dichloromethane and trichloromethane.
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