CN114560897B - Post-treatment method for preparing fully-benzoylated glucose - Google Patents
Post-treatment method for preparing fully-benzoylated glucose Download PDFInfo
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- CN114560897B CN114560897B CN202210358700.2A CN202210358700A CN114560897B CN 114560897 B CN114560897 B CN 114560897B CN 202210358700 A CN202210358700 A CN 202210358700A CN 114560897 B CN114560897 B CN 114560897B
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- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 title claims abstract description 46
- 239000008103 glucose Substances 0.000 title claims abstract description 46
- 238000000034 method Methods 0.000 title claims abstract description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 100
- 238000006243 chemical reaction Methods 0.000 claims abstract description 79
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 78
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 claims abstract description 53
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 48
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 31
- 238000001704 evaporation Methods 0.000 claims abstract description 18
- 238000005406 washing Methods 0.000 claims abstract description 18
- 238000001914 filtration Methods 0.000 claims abstract description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims abstract description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 14
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000001514 detection method Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract description 5
- 239000002351 wastewater Substances 0.000 abstract description 4
- 238000009776 industrial production Methods 0.000 abstract description 3
- 239000002253 acid Substances 0.000 abstract description 2
- 239000011230 binding agent Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 238000000605 extraction Methods 0.000 description 10
- 230000008020 evaporation Effects 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 150000004676 glycans Chemical class 0.000 description 4
- 229920001282 polysaccharide Polymers 0.000 description 4
- 239000005017 polysaccharide Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229920001503 Glucan Polymers 0.000 description 2
- -1 ethyl acetate compound Chemical class 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 238000005285 chemical preparation method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/84—Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/86—Separation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Abstract
The invention relates to a post-treatment method for synthesizing full benzoyl protected glucose. The full benzoyl protection of glucose uses benzoyl chloride as raw material, triethylamine as acid-binding agent, and after the reaction is completed, the reaction system contains a large quantity of triethylamine hydrochloride. The invention provides a post-treatment method, glucose is dissolved by DMF, triethylamine and benzoyl chloride with a proportion are added, ethyl acetate with the volume of 4-5 times is added into a reaction system after the reaction is finished, so that triethylamine hydrochloride is separated out, filtration is carried out, and crude triethylamine hydrochloride is washed by ethyl acetate, thus obtaining pure triethylamine hydrochloride; and evaporating the reaction system, adding dichloromethane into the reaction system, and then, extracting and washing with 1N hydrochloric acid, saturated sodium bicarbonate and saturated sodium chloride, and evaporating to dryness to obtain the full benzoylated glucose. The treatment method can recycle triethylamine hydrochloride, reduce the content of organic matters in the wastewater, and is suitable for industrial production.
Description
Technical Field
The invention relates to a post-treatment method for preparing full benzoylated glucose.
Background
The glucan has biological activities of resisting tumor, inflammation, bacteria, viruses, blood fat and the like, and is now receiving more and more attention. The common structural feature of these biologically active polysaccharides is the glucan oligosaccharides containing a beta- (1→6) branched beta- (1→3) backbone. As the polysaccharide prepared by the chemical synthesis method has definite molecular weight and structure and controllable quality, the polysaccharide prepared by the method has higher curative effect than the polysaccharide prepared by the extraction method and the enzymatic method, more scientists search for a chemical preparation method capable of being industrialized.
The benzoyl is stable, the prepared full benzoyl glucose is easy to dry, orthoesters are not easy to generate during the synthesis of glycosidic bonds, and the coupling process has higher yield. The full benzoyl protection of glucose uses benzoyl chloride as raw material, triethylamine as acid-binding agent, and after the reaction is completed, the reaction system contains a large quantity of triethylamine hydrochloride. The common post-treatment mode is to directly use dilute hydrochloric acid, saturated sodium bicarbonate and saturated sodium chloride for extraction and wash, and discard triethylamine hydrochloride as waste, thereby increasing the wastewater and waste liquid treatment burden of enterprises.
Disclosure of Invention
The invention aims to provide a post-treatment method for preparing full-benzoylated glucose, which is used for recycling triethylamine hydrochloride, reducing the content of organic matters in wastewater and is suitable for industrial production.
In order to solve the technical problems of the invention, the technical proposal is as follows: after dissolving glucose in DMF, adding a certain amount of benzoyl chloride and triethylamine, detecting the end of the reaction to prepare the fully benzoylated glucose, adding ethyl acetate with the volume of more than 4 times that of the triethylamine into a reaction system to separate out triethylamine hydrochloride, filtering, and washing the crude triethylamine hydrochloride with ethyl acetate to obtain pure triethylamine hydrochloride; evaporating the reaction system, adding dichloromethane into the reaction system, then extracting and washing with hydrochloric acid, saturated sodium bicarbonate and saturated sodium chloride, and evaporating to dryness to obtain the full benzoylated glucose.
Preferably, glucose, benzoyl chloride and triethylamine are added in a molar ratio of 1:5.4:5.2 protecting all hydroxyl groups of glucose with benzoyl groups.
Preferably, the volume ratio of the added ethyl acetate to the added triethylamine is 4-5:1.
preferably, the triethylamine hydrochloride obtained by filtration is washed with ethyl acetate for 2-3 times to obtain the triethylamine hydrochloride with high purity.
Preferably, the hydrochloric acid is 1mol/L hydrochloric acid.
Preferably, after glucose is dissolved in DMF, a certain amount of benzoyl chloride and triethylamine are added, and the molar ratio of the added glucose to the benzoyl chloride to the triethylamine is 1:5.4:5.2, after the detection reaction is finished, preparing fully benzoylated glucose, adding ethyl acetate into a reaction system, wherein the volume ratio of the added ethyl acetate to the added triethylamine is 5:1, precipitating triethylamine hydrochloride, filtering, washing crude triethylamine hydrochloride with ethyl acetate for 2-3 times to obtain pure triethylamine hydrochloride; evaporating the reaction system, adding dichloromethane into the reaction system, then extracting and washing with 1mol/L hydrochloric acid, saturated sodium bicarbonate and saturated sodium chloride, and evaporating to dryness to obtain the full benzoylated glucose.
Glucose is dissolved by DMF, triethylamine (5.4 eq) and benzoyl chloride (5.2 eq) are added in proportion, ethyl acetate is added into a reaction system after the reaction is finished, triethylamine hydrochloride is separated out, the reaction system is evaporated to dryness, dichloromethane is added into the reaction system, 1N hydrochloric acid, saturated sodium bicarbonate and saturated sodium chloride are used for extraction and washing, and the fully benzoylated glucose is obtained after evaporation to dryness.
The beneficial effects are that:
the invention provides a post-treatment method, glucose is dissolved by DMF, a proportional amount of triethylamine (5.4 eq) and benzoyl chloride (5.2 eq) are added, ethyl acetate is added into a reaction system after the reaction is finished, triethylamine hydrochloride is separated out, filtration is carried out, crude triethylamine hydrochloride is washed by ethyl acetate, pure triethylamine hydrochloride is obtained, the reaction system is evaporated to dryness, dichloromethane is added into the reaction system, hydrochloric acid, saturated sodium bicarbonate and saturated sodium chloride are used for extraction and washing, and the fully benzoylated glucose is obtained after evaporation to dryness. The treatment method can recycle triethylamine hydrochloride, has little organic matter content in the wastewater, and is suitable for industrial production.
The inventor uses a compound solvent of dichloromethane, cyclohexane or ethyl acetate to separate out triethylamine hydrochloride, but the salt precipitation effect is not ideal compared with the effect of using ethyl acetate. The inventor adds ethyl acetate into the reaction system to separate out triethylamine hydrochloride, the prior art does not teach the method, and can realize that the triethylamine hydrochloride is separated out unexpectedly, and no other impurity salt is separated out, the purity of the obtained triethylamine hydrochloride reaches 99.8%, the yield reaches 99.5%, the purpose of recycling the triethylamine hydrochloride can be realized, the production cost is saved, the wastewater treatment cost is reduced, and the environmental pollution is reduced.
By changing the volume ratio of the added ethyl acetate to the added triethylamine, the optimal volume ratio is unexpectedly found to be 5:1, and the purity of the obtained triethylamine hydrochloride reaches 99.8 percent, and the yield reaches 99.5 percent. As can be seen from comparative example 3 or comparative example 4, the amount of addition was 3 times (V: V) the amount of triethylamine added in the reaction, and the purity of the obtained triethylamine hydrochloride reached 88.6% and the yield reached 62.4%. The addition amount is more than 5 times of the amount of triethylamine added in the reaction, the purity and the yield are also reduced, and the use amount of ethyl acetate is increased.
Detailed Description
The following specific embodiments are used to illustrate the technical solution of the present invention, but the scope of the present invention is not limited thereto: example 1
Preparation of fully benzoylated glucose
80mL of DMF was placed in a 500mL flask, heated to 70℃and glucose (10 g,55.56 mmol) was added until all dissolved, and triethylamine (41.70 mL,300.0 mmol) was added. After the flask was taken out and cooled to room temperature, the reaction system was placed in an ice bath, benzoyl chloride (33.27 mL,288.89 mmol) was added dropwise, and after the completion of the addition, the reaction system was allowed to return to room temperature, and was stirred with heating in an oil bath at 70℃for 24 hours. TLC detection reaction completion (8%H) 2 SO 4 -carbonization of EtOH solution), rf:0.62 (cyclohexane: ethyl acetate=3:1).
Post-treatment method for preparing fully benzoylated glucose
(1) After the reaction of the fully benzoylated glucose is finished, ethyl acetate is added into the reaction system, the addition amount is 4 times (V: V) of the amount of triethylamine added in the reaction, triethylamine hydrochloride is separated out, the reaction system is filtered and evaporated to dryness, 80mL of dichloromethane is added into the reaction system, and then 40mL of 1N hydrochloric acid (2 times), saturated sodium bicarbonate (2 times) and saturated sodium chloride are used for extraction and washing (1 time), and the fully benzoylated glucose is obtained after evaporation to dryness.
The triethylamine hydrochloride obtained by filtration is washed by ethyl acetate for 2 to 3 times, and the purity of the obtained triethylamine hydrochloride reaches 99.4 percent, and the yield reaches 99.1 percent.
Example 2
After the reaction of the fully benzoylated glucose is finished, ethyl acetate is added into the reaction system, the addition amount is 4.5 times (V: V) of the amount of triethylamine added in the reaction, triethylamine hydrochloride is separated out, the reaction system is filtered and evaporated to dryness, 80mL of dichloromethane is added into the reaction system, and then 40mL of 1N hydrochloric acid (2 times), saturated sodium bicarbonate (2 times) and saturated sodium chloride are used for extraction and washing (1 time), and the fully benzoylated glucose is obtained after evaporation to dryness.
The triethylamine hydrochloride obtained by filtration is washed by ethyl acetate for 2 to 3 times, and the purity of the obtained triethylamine hydrochloride reaches 99.6 percent and the yield reaches 99.5 percent.
Example 3
After the reaction of the fully benzoylated glucose is finished, ethyl acetate is added into the reaction system, the addition amount is 5 times (V: V) of the amount of triethylamine added in the reaction, triethylamine hydrochloride is separated out, the reaction system is filtered and evaporated to dryness, 80mL of dichloromethane is added into the reaction system, and then 40mL of 1N hydrochloric acid (2 times), saturated sodium bicarbonate (2 times) and saturated sodium chloride are used for extraction and washing (1 time), and the fully benzoylated glucose is obtained after evaporation to dryness.
The triethylamine hydrochloride obtained by filtration is washed by ethyl acetate for 2 to 3 times, and the purity of the obtained triethylamine hydrochloride reaches 99.8 percent, and the yield reaches 99.5 percent.
From the above examples, it was found that the triethylamine hydrochloride obtained by adding ethyl acetate in an amount of 5 times of triethylamine (V: V) into the reaction system having completed the reaction had a high purity and a high yield, and was the best post-treatment method.
Comparative example 1
After the reaction of the fully benzoylated glucose is finished, methylene dichloride is added into a reaction system, the addition amount of the methylene dichloride is 5 times (V: V) of the amount of triethylamine added in the reaction, triethylamine hydrochloride is separated out, the reaction system is filtered and evaporated to dryness, 80mL of methylene dichloride is added into the reaction system, and then 40mL of 1N hydrochloric acid (2 times), saturated sodium bicarbonate (2 times) and saturated sodium chloride are used for extraction and washing (1 time), and the fully benzoylated glucose is obtained after evaporation to dryness.
The triethylamine hydrochloride obtained by filtration is washed by dichloromethane for 2 to 3 times, the purity of the obtained triethylamine hydrochloride reaches 45.6 percent, and the yield reaches 52.3 percent.
Comparative example 2
After the reaction of the fully benzoylated glucose is finished, adding a cyclohexane and ethyl acetate compound solvent (cyclohexane: ethyl acetate=1:3) into a reaction system, wherein the addition amount is 5 times (V: V) of the amount of triethylamine added in the reaction, separating out triethylamine hydrochloride, filtering, evaporating the reaction system to dryness, adding 80mL of dichloromethane into the reaction system, and then extracting and washing with 40mL of 1N hydrochloric acid (2 times), saturated sodium bicarbonate (2 times) and saturated sodium chloride (1 time), and evaporating to dryness to obtain the fully benzoylated glucose.
The triethylamine hydrochloride obtained by filtration is washed for 2 to 3 times by a cyclohexane and ethyl acetate compound solvent, and the purity of the obtained triethylamine hydrochloride reaches 68.1 percent, and the yield reaches 71.5 percent.
Comparative example 3
After the reaction of the fully benzoylated glucose is finished, ethyl acetate is added into the reaction system, the addition amount is 6 times (V: V) of the amount of triethylamine added in the reaction, triethylamine hydrochloride is separated out, the reaction system is filtered and evaporated to dryness, 80mL of dichloromethane is added into the reaction system, and then 40mL of 1N hydrochloric acid (2 times), saturated sodium bicarbonate (2 times) and saturated sodium chloride are used for extraction and washing (1 time), and the fully benzoylated glucose is obtained after evaporation to dryness.
The triethylamine hydrochloride obtained by filtration is washed by ethyl acetate for 2 to 3 times, and the purity of the obtained triethylamine hydrochloride reaches 99.7 percent, and the yield reaches 99.5 percent.
Comparative example 4
After the reaction of the fully benzoylated glucose is finished, ethyl acetate is added into the reaction system, the addition amount is 3 times (V: V) of the amount of triethylamine added in the reaction, triethylamine hydrochloride is separated out, the reaction system is filtered and evaporated to dryness, 80mL of dichloromethane is added into the reaction system, and then 40mL of 1N hydrochloric acid (2 times), saturated sodium bicarbonate (2 times) and saturated sodium chloride are used for extraction and washing (1 time), and the fully benzoylated glucose is obtained after evaporation to dryness.
The triethylamine hydrochloride obtained by filtration is washed by ethyl acetate for 2 to 3 times, and the purity of the obtained triethylamine hydrochloride reaches 88.6 percent and the yield reaches 62.4 percent.
The foregoing examples are preferred embodiments of the present invention, but the embodiments of the present invention are not limited to the foregoing examples, and any other modifications that do not depart from the present invention should be equivalent to the above-described examples, and are included in the scope of the present invention.
Claims (1)
1. A post-treatment method for preparing fully benzoylated glucose is characterized by comprising the following steps: the preparation of the fully benzoylated glucose is as follows: 80mL of DMF was placed in a 500mL flask, heated to 70℃and 10g of glucose was added until all dissolved, 41.70mL,300.0mmol of triethylamine was added; taking out the flask, cooling to room temperature, placing the reaction system in an ice bath, dropwise adding 33.27mL and 288.89mmol benzoyl chloride, after the dropwise adding is finished, returning the reaction system to the room temperature, heating and stirring in an oil bath at 70 ℃, and reacting for 24 hours; TLC detection reaction is finished;
the post-treatment method for preparing the full benzoylated glucose comprises the following steps:
after the reaction of the fully benzoylated glucose is finished, adding ethyl acetate into a reaction system, wherein the addition amount is 5 times of the volume of the amount of triethylamine added in the reaction, separating out triethylamine hydrochloride, filtering, evaporating the reaction system, washing the reaction system with 80mL of dichloromethane, washing the reaction system with 40mL of 1N hydrochloric acid for 2 times, washing the reaction system with saturated sodium bicarbonate for 2 times, washing the reaction system with saturated sodium chloride for 1 time, and evaporating the reaction system to obtain the fully benzoylated glucose;
the triethylamine hydrochloride obtained by filtration is washed by ethyl acetate for 2 to 3 times, and the purity of the obtained triethylamine hydrochloride reaches 99.8 percent, and the yield reaches 99.5 percent.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1290705A (en) * | 1999-09-30 | 2001-04-11 | 中国科学院生态环境研究中心 | Synthesizing method of 1-hydroxy monosaccharide benzoylate |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1290705A (en) * | 1999-09-30 | 2001-04-11 | 中国科学院生态环境研究中心 | Synthesizing method of 1-hydroxy monosaccharide benzoylate |
Non-Patent Citations (3)
| Title |
|---|
| Effects of Tannins from Geum japonicum on the Catalytic Activity of Thrombin and Factor Xa of Blood Coagulation Cascade;Dong, Hui 等;《Journal of Natural Products》;第61卷(第11期);第1356-1360页 * |
| Selective benzoylation of monosaccharides;Batey, John F 等;《Carbohydrate Research》;第43卷(第1期);第43-50页 * |
| 单体活性给体合成方法的改进;郑利刚 等;《沈阳药科大学学报》;第22卷(第5期);第352-354页 * |
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