CN103709210B - The preparation technology of isopropyl-β-D-thiogalactoside - Google Patents
The preparation technology of isopropyl-β-D-thiogalactoside Download PDFInfo
- Publication number
- CN103709210B CN103709210B CN201310671072.4A CN201310671072A CN103709210B CN 103709210 B CN103709210 B CN 103709210B CN 201310671072 A CN201310671072 A CN 201310671072A CN 103709210 B CN103709210 B CN 103709210B
- Authority
- CN
- China
- Prior art keywords
- isopropyl
- adds
- thiogalactoside
- galactose
- reacted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Landscapes
- Saccharide Compounds (AREA)
Abstract
The present invention relates to sugar compounds field, be specifically related to the preparation technology of a kind of isopropyl ss D thiogalactoside.Room temperature adds acetic anhydride and catalyst, adds galactose, after having reacted, adds isopropyl mercaptan, processes through later and obtain isopropylthio acetyl galactose after having reacted.It is added to isopropylthio acetyl galactose in methanol dissolve, adds Feldalat NM, add acetic acid after having reacted and neutralize, obtain isopropyl ss D thiogalactoside through post processing.The inventive method passes through two-step reaction method synthetic isopropyl β D thiogalactoside, and simple to operate, raw material is easy to get, and has saved running cost and material.
Description
Technical field
The present invention relates to sugar compounds field, be specifically related to the preparation technology of a kind of isopropyl-β-D-thiogalactoside.
Background technology
Isopropyl-β-D-thiogalactoside, also known as IPTG, English name: Isopropyl β-D-1-
Thiogalactopyranoside, No. CAS: 367-93-1, molecular formula C9H18O5S。
In the prior art, general employing galactose and acetic anhydride react preparation five acetyl galas under the effect of sodium acetate
Sugar, five acetyl galactose are dissolved under catalyst and isopropyl mercaptan reaction preparation four acetyl isopropylthio galactose, tetrem
Acyl isopropylthio galactose is through the deacetylated isopropyl-β-D-thiogalactoside of preparing of Feldalat NM, and this method is first prepared
Five acetyl galactose, then purify cause certain raw materials consumption, operate comparatively laborious, relatively costly.Such as patent:
201210553464, another kind of method is to react generation galactose isothiourea fluoro with penta-acetyl galactose for raw material and thiourea
Salt, galactose isothiourea fluoro salt generates isopropyl-beta D-thio four acetylglactoside with different bromopropane reaction, then takes off second
Acyl obtains isopropyl-β-D-thiogalactoside, and this route steps is many, operation complexity, relatively costly, such as patent:
201310010582.7。
Summary of the invention
Compare to solve in above prior art cost present in the preparation of isopropyl-β-D-thiogalactoside
Height, operates more numerous and diverse, and yield, than relatively low present situation, the invention provides and a kind of uses two-step method, simple to operate, raw material to be easy to get
The preparation technology of isopropyl-β-D-thiogalactoside.
The present invention is achieved by the following measures:
The preparation technology of a kind of isopropyl-β-D-thiogalactoside, comprises the following steps:
A) room temperature adds acetic anhydride and catalyst, point 9 batches of addition galactose, after having reacted, adds isopropyl mercaptan, has reacted
Process after Cheng Houjing and obtain isopropylthio acetyl galactose；
B) it is added to isopropylthio acetyl galactose in methanol dissolve, adds Feldalat NM, after having reacted, add vinegar
Acid neutralizes, and obtains isopropyl-β-D-thiogalactoside through post processing；
Acetic anhydride in step a: catalyst: galactose: the mol ratio of isopropyl mercaptan is 6: 1.5: 1:1.2.
Described method, isopropylthio acetyl galactose: the mol ratio of Feldalat NM is 1:0.01-0.06.
Described method, in step a, reaction temperature is 5-10 DEG C.
Described method, in step a, catalyst is aluminum chloride, ferric chloride, zinc chloride.
Described method, in step a, the response time is 16-24 hour, and in step b, the response time is 2-4 hour.
Described method, in step a, post processing is cancellation, extraction, and washing concentrates, and adds mixed solvent crystallization.
Described method, in step b, post processing is for being concentrated to dryness, and adds mixed solvent crystallize.
In described method step a, mixed solvent be mol ratio be the mixed of the t-butyl methyl ether of 1:2-3 and isohexane
And solvent.
Described method, in step b, mixed solvent be mol ratio be ethanol and the mixing of t-butyl methyl ether of 1:5-10
Solvent.
Beneficial effect: the inventive method uses different reaction systems, including catalyst, processing method etc., only by two
Step reaction obtains product, is effectively improved safety coefficient and product；Simple to operate, raw material is easy to get, and has saved running cost and thing
Material.
Detailed description of the invention
In order to further understand the present invention, below in conjunction with specific embodiment, the process of this programme is described, but
Should be appreciated that these describe be intended merely to further instruction the features and advantages of the present invention rather than right of the present invention is wanted
The restriction asked.
Embodiment 1
A) room temperature adds 6mol acetic anhydride and 1.5mol aluminum chloride, adds 1mol galactose, reaction at 5-10 DEG C point 12 batches
After completing, add 1.3mol isopropyl mercaptan, process through later after having reacted and obtain 0.774mol isopropylthio acetyl gala
Sugar；
B) it is added to 0.774mol isopropylthio acetyl galactose in 10mol methanol dissolve, adds 0.01mol methanol
Sodium, adds 0.01mol acetic acid and neutralizes, obtain 0.756mol IPTG through post processing after having reacted
Glycosides.Yield is 75.6%.
In step a, post processing is that the water of dropping 0-5 DEG C of 10mol stirs 2 hours, with the extraction of the dichloromethane of 5mol
Water layer, separates organic facies 10mol water washing organic facies three times, separates organic facies and concentrate, add 1mol t-butyl methyl ether and
The isohexane mixed liquor crystallization of 2mol, filters, is dried.
In step b, post processing is for being concentrated to dryness, and adds 0.2mol ethanol and the crystallize of 1.8mol t-butyl methyl ether, filters,
It is dried.
Comparative examples
A) room temperature adds 15mol acetic anhydride and 0.15mol sodium acetate, point 12 batches of addition 1mol galactose under condensing reflux,
After having reacted, add 100mol water, separate out yellow scape solid, through 5mol ethanol be recrystallized to give 0.51mol's
Five acetyl galactose；
B) five acetyl galactose of 0.51moll are added in the dichloromethane of 10mol, add the boron trifluoride of 0.75mol
Ether, adds the isopropyl mercaptan of 1.25mol, stirs 2 hours, reacted rear post processing and obtained the different of 0.453mol at 0-5 DEG C
Propyl dithiocarbamate acetyl galactose；
C) it is added to 0.453mol isopropylthio acetyl galactose in 10mol methanol dissolve, adds 0.01mol methanol
Sodium, adds 0.01mol acetic acid and neutralizes, obtain 0.452mol IPTG through post processing after having reacted
Glycosides.Yield is 45.2%.
In step b, post processing is that the water of dropping 0-5 DEG C of 10mol stirs 2 hours, with the extraction of the dichloromethane of 5mol
Water layer, separates organic facies 10mol water washing organic facies three times, separates organic facies and concentrate, add 0.5mol t-butyl methyl ether
Crystallize with the isohexane mixed liquor of 1mol, filter, be dried.
Claims (1)
1. a preparation technology for isopropyl-β-D-thiogalactoside, is characterized in that comprising the following steps:
A) room temperature adds 6mol acetic anhydride and 1.5mol aluminum chloride, adds 1mol galactose at 5-10 DEG C point 12 batches, and reaction completes
After, add 1.3mol isopropyl mercaptan, process through later after having reacted and obtain 0.774mol isopropylthio acetyl galactose；
B) it is added to 0.774mol isopropylthio acetyl galactose in 10mol methanol dissolve, adds 0.01mol Feldalat NM,
Add 0.01mol acetic acid after having reacted to neutralize, obtain 0.756mol isopropyl-β-D-thiogalactoside through post processing,
Yield is 75.6%;
In step a, post processing is that the water of dropping 0-5 DEG C of 10mol stirs 2 hours, extracts extraction water with the dichloromethane of 5mol
Layer, separates organic facies 10mol water washing organic facies three times, separates organic facies and concentrate, add 1mol t-butyl methyl ether and
The isohexane mixed liquor crystallization of 2mol, filters, is dried;
In step b, post processing is for being concentrated to dryness, and adds 0.2mol ethanol and the crystallize of 1.8mol t-butyl methyl ether, filters, and is dried.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310671072.4A CN103709210B (en) | 2013-12-12 | 2013-12-12 | The preparation technology of isopropyl-β-D-thiogalactoside |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310671072.4A CN103709210B (en) | 2013-12-12 | 2013-12-12 | The preparation technology of isopropyl-β-D-thiogalactoside |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103709210A CN103709210A (en) | 2014-04-09 |
| CN103709210B true CN103709210B (en) | 2016-08-17 |
Family
ID=50402598
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310671072.4A Active CN103709210B (en) | 2013-12-12 | 2013-12-12 | The preparation technology of isopropyl-β-D-thiogalactoside |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103709210B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105566410A (en) * | 2016-02-26 | 2016-05-11 | 宁波欧曼生物科技有限公司 | Preparation method for isopropyl-beta-D-thiogalactopyranoside |
| CN108299524B (en) * | 2018-01-09 | 2021-03-02 | 苏州亚科科技股份有限公司 | Preparation method of isopropyl-beta-D-thiogalactopyranoside intermediate |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004076477A1 (en) * | 2003-02-26 | 2004-09-10 | Holland Sweetener Company | MICROBIOLOGICAL PRODUCTION METHOD FOR α-L-ASPARTYL-L-PHENYLALANINE |
| CN102070676A (en) * | 2009-11-20 | 2011-05-25 | 中国科学院成都生物研究所 | Method for preparing 2-C-acetonyl-2-deoxy-D-galactopyranose and derivatives of 2-C-acetonyl-2-deoxy-D-galactopyranose |
| CN102993246A (en) * | 2012-12-19 | 2013-03-27 | 北京利德曼生化股份有限公司 | Method for synthesizing isopropyl-beta-D-thiogalactoside |
-
2013
- 2013-12-12 CN CN201310671072.4A patent/CN103709210B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004076477A1 (en) * | 2003-02-26 | 2004-09-10 | Holland Sweetener Company | MICROBIOLOGICAL PRODUCTION METHOD FOR α-L-ASPARTYL-L-PHENYLALANINE |
| CN102070676A (en) * | 2009-11-20 | 2011-05-25 | 中国科学院成都生物研究所 | Method for preparing 2-C-acetonyl-2-deoxy-D-galactopyranose and derivatives of 2-C-acetonyl-2-deoxy-D-galactopyranose |
| CN102993246A (en) * | 2012-12-19 | 2013-03-27 | 北京利德曼生化股份有限公司 | Method for synthesizing isopropyl-beta-D-thiogalactoside |
Non-Patent Citations (1)
| Title |
|---|
| Concise syntheses of arabinogalactans with b-(1!6)-linked galactopyranose backbones and a-(1!3)- and a-(1!2)-linked arabinofuranose side chains;Aixiao Li，等;《Bioorganic & Medicinal Chemistry》;20051231;第13卷(第3期);第839-853页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103709210A (en) | 2014-04-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103709209B (en) | The preparation method of isopropyl-β-D-thiogalactoside | |
| CN102395591B (en) | Method for preparing prasugrel | |
| CN106748921B (en) | A kind of virtue sulfuryl difluoroacetic acid salt compounds, preparation method and applications | |
| CN104292285A (en) | Process for synthesizing high-content dehydronandrolon acetate | |
| CN103709210B (en) | The preparation technology of isopropyl-β-D-thiogalactoside | |
| CN103601766B (en) | Fondaparinux sodium pentasaccharide intermediate and preparation method thereof | |
| CN104402909A (en) | Synthetic method of cefoxitin acid | |
| CN103665063B (en) | A kind of method preparing isopropyl-β-D-thiogalactoside(IPTG) | |
| CN106699586A (en) | Preparation method of ornithine aspartate | |
| CN108929348A (en) | The preparation method of isopropyl-β-D thiogalactoside | |
| CN102924346B (en) | Method for synthesizing methyl sulfone base dibromo toluene | |
| CN103694285B (en) | A kind of preparation method of isopropyl-β-D-thiogalactoside(IPTG) | |
| CN103694284B (en) | A kind of preparation technology of isopropyl-β-D-thiogalactoside(IPTG) | |
| CN103694286B (en) | Prepare the method for isopropyl-β-D-thiogalactoside(IPTG) | |
| CN101381297B (en) | Method for separating caprylic acid from mixture of caprylic acid and capric acid | |
| CN103665064B (en) | One prepares the method for 2,3,4,6-, tetra--oxygen-benzyl-D-galactopyranose | |
| CN103626695B (en) | New method for preparing fluazinam by using mixed solvent as medium | |
| CN102070587B (en) | One kettle way prepares the method for Simvastatin | |
| CN103232506B (en) | The preparation technology of clarithromycin impurity O and similar compound thereof | |
| CN101974021B (en) | Method for synthesizing cefuroxime acid | |
| CN105330525A (en) | Preparation method of 7-hydroxy-1-indanone | |
| CN103694288B (en) | The method of preparation 2,3,4,6-tetra--oxygen-benzyl-D-galactopyranose | |
| CN103588825A (en) | Method for protecting D-glucosamine derivative by using benzaldehyde dimethyl acetal | |
| CN102942602B (en) | The preparation method of o-nitrophenyl galactoside | |
| CN109942659B (en) | Synthetic method of betamethasone intermediate |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| CB02 | Change of applicant information |
Address after: Shengquan Industrial Park 250204 Shandong city of Ji'nan province Zhangqiu City Diao Town Industrial Development Zone Applicant after: CARBOTANG BIOTECH CO.,LTD. Address before: Shengquan Industrial Park 250204 Shandong city of Ji'nan province Zhangqiu City Diao Town Industrial Development Zone Applicant before: CARBOTANG LTD. |
|
| COR | Change of bibliographic data | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CP03 | Change of name, title or address | ||
| CP03 | Change of name, title or address |
Address after: 250204 Diaozhen Street Chemical Industrial Park, Zhangqiu District, Jinan City, Shandong Province Patentee after: Jinan Carbotang Biotech Co.,Ltd. Address before: 250204 Shengquan Industrial Park, Diaozhen Industrial Development Zone, Zhangqiu City, Jinan City, Shandong Province Patentee before: CARBOTANG BIOTECH CO.,LTD. |