CN108084234A - The method that dual random glycosyl is combined to trisaccharide - Google Patents
The method that dual random glycosyl is combined to trisaccharide Download PDFInfo
- Publication number
- CN108084234A CN108084234A CN201810061764.XA CN201810061764A CN108084234A CN 108084234 A CN108084234 A CN 108084234A CN 201810061764 A CN201810061764 A CN 201810061764A CN 108084234 A CN108084234 A CN 108084234A
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- Prior art keywords
- random
- trisaccharide
- combined
- glycosyl
- mixture
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/18—Acyclic radicals, substituted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
Abstract
The present invention relates to the methods that dual random glycosyl is combined to trisaccharide.The present invention has been combined to trisaccharide using monose as raw material, by dual random glycosyl.First random glycosyl has been combined to the mixture of 6 kinds of disaccharides, and second of random glycosyl has been combined to the mixture of 36 trisaccharides.The method that dual random glycosyl of the present invention is combined to trisaccharide has substantially saved the time synthesized and cost, and a kind of new approaches are provided for the synthesis of complex oligosaccharide.
Description
Technical field
The present invention relates to the methods that dual random glycosyl is combined to trisaccharide.
Background technology
Glycoconjugate plays important work in cell recognition, adherency, cell cycle regulation, cancer metastasis and inflammation
With.The carbohydrate of cell surface can cause to fall ill as the anchored site of infectious bacteria, virus and toxin.Therefore, newly
The synthesis of type carbohydrate and its inhibitor for contributing to find some key pathogenetic processes to the screening of virulence factor.So
And the chemical synthesis of carbohydrate is time-consuming and laborious, and technology requirement is very high.Therefore need to find more effective synthetic method to come very
Support oligosaccharides.
Random glycosylation strategy is proved to be the excellent combinatorial compound method for generating oligosaccharides.The strategy eliminates the need for structure
Many synthesis steps of the sugar structure module of orthogonal protection are built, and reduce time and the cost of synthesis.Pass through dual random
Glycosylation process, being capable of synthesis of oligose in an efficient way.
The content of the invention
The present invention has been combined to trisaccharide using monose as raw material, by dual random glycosyl.The method of the present invention is substantially saved
The time of synthesis and cost, the synthesis for the oligosaccharides of complexity provide a kind of new approaches.
The present invention is achieved by the following technical solutions：
The method that dual random glycosyl is combined to trisaccharide, comprises the following steps：
(1) random glycosylation for the first time
Compound 1 and compound 2 are dissolved in dioxane, then add in boron trifluoride ether, react at room temperature to
Completely；Using palladium carbon as catalyst, the product after reaction is led into hydrogen reducing；
(2) second of random glycosylation
Product after reduction is dissolved in anhydrous DMF, adds in the anhydrous CaSO of powdery4With compound 3, lead to condition of nitrogen gas
Under, by mixture be stirred at room temperature reaction 2 it is small when；Add in boron trifluoride ether chloroform soln after, at room temperature after
It is continuous be stirred to react 10 it is small when；Triethylamine is added to be purified after stopping reaction, the product after purification is dissolved in the mixing of methanol and acetic acid
In object, lead to hydrogen reducing with diatomite, up to the glycosylated trisaccharide of dual random after purification.
Preferably, the molar ratio of compound 1 and compound 2 is 1:1.
Preferably, the product for the first time after random glycosylation is the mixture of 6 kinds of disaccharides.
Preferably, the dosage of compound 3 is 4 times of 1 mole of compound.
Preferably, the mixture of the methanol and acetic acid is methanol and acetic acid volume ratio 5:1 mixture.
Preferably, the product after second of random glycosylation is the mixture of 36 kinds of trisaccharides.
Beneficial effects of the present invention：
The present invention has been combined to trisaccharide using monose as raw material, by dual random glycosyl.The method of the present invention is substantially saved
The time of synthesis and cost, for the synthesis of complex oligosaccharide provide a kind of new approaches.
Specific embodiment
Below in conjunction with specific embodiment, the invention will be further described.
(1) random glycosylation for the first time
Compound 1 (0.5mmol) and compound 2 (0.5mmol) are dissolved in dioxane (10mL), then add in trifluoro
Change borate ether (1mL), reaction 10h is stirred at room temperature to complete；After evaporation of solvent, residue is dissolved in methanol
In (10mL), add in catalyst palladium carbon (100mg), lead to hydrogen reducing 3 it is small when；
(2) second of random glycosylation
Product after reduction is dissolved in anhydrous DMF (20mL), adds in the anhydrous CaSO of powdery4(200mg) and chemical combination
Object 3 (2mmol), lead to condition of nitrogen gas under, by mixture be stirred at room temperature reaction 2 it is small when；Add in boron trifluoride ether (1mL)
After chloroform soln (10mL), continue to be stirred to react at room temperature 10 it is small when；Triethylamine (0.1mL) is added to stop reaction, decompression
Solvent is distilled off, residue is purified by silica gel column chromatography, and eluent is dichloromethane and methanol volume ratio 10:1 mixing
Object：Product after purification is dissolved in methanol and acetic acid volume ratio 5:In 1 mixture, diatomite (100mg) is added in, leads to hydrogen
Reduction, up to the glycosylated trisaccharide of dual random, yield 30% after purification.
Claims (6)
1. the method that dual random glycosyl is combined to trisaccharide, which is characterized in that comprise the following steps：
(1) random glycosylation for the first time
Compound 1 and compound 2 are dissolved in dioxane, then add in boron trifluoride ether, is reacted at room temperature to complete；
Using palladium carbon as catalyst, the product after reaction is led into hydrogen reducing；
(2) second of random glycosylation
Product after reduction is dissolved in anhydrous DMF, adds in the anhydrous CaSO of powdery4With compound 3, lead under condition of nitrogen gas, it will
Mixture be stirred at room temperature reaction 2 it is small when；After adding in the chloroform soln of boron trifluoride ether, continue to stir at room temperature
React 10 it is small when；Triethylamine is added to be purified after stopping reaction, the product after purification is dissolved in the mixture of methanol and acetic acid, is used
Diatomite leads to hydrogen reducing, up to the glycosylated trisaccharide of dual random after purification.
2. the method that dual random glycosyl according to claim 1 is combined to trisaccharide, which is characterized in that compound 1 is with changing
The molar ratio for closing object 2 is 1:1.
3. the method that dual random glycosyl according to claim 1 is combined to trisaccharide, which is characterized in that random sugar for the first time
Product after base is the mixture of 6 kinds of disaccharides.
4. the method that dual random glycosyl according to claim 1 is combined to trisaccharide, which is characterized in that the use of compound 3
It measures as 4 times of 1 mole of compound.
5. the method that dual random glycosyl according to claim 1 is combined to trisaccharide, which is characterized in that the methanol and second
The mixture of acid is methanol and acetic acid volume ratio 5:1 mixture.
6. the method that dual random glycosyl according to claim 1 is combined to trisaccharide, which is characterized in that second of random sugar
Product after base is the mixture of 36 kinds of trisaccharides.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810061764.XA CN108084234A (en) | 2018-01-23 | 2018-01-23 | The method that dual random glycosyl is combined to trisaccharide |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201810061764.XA CN108084234A (en) | 2018-01-23 | 2018-01-23 | The method that dual random glycosyl is combined to trisaccharide |
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| Publication Number | Publication Date |
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| CN108084234A true CN108084234A (en) | 2018-05-29 |
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| CN201810061764.XA Pending CN108084234A (en) | 2018-01-23 | 2018-01-23 | The method that dual random glycosyl is combined to trisaccharide |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109021036A (en) * | 2018-08-13 | 2018-12-18 | 佛山科学技术学院 | The method that α-connection disaccharides is combined to by the random glycosyl of unprotected monosaccharide |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996006102A1 (en) * | 1994-08-24 | 1996-02-29 | Ciba-Geigy Ag | Process for the preparation of oligosaccharide mixtures |
| CN102212087A (en) * | 2011-01-24 | 2011-10-12 | 南京工业大学 | Method for preparing 3,6-branched triglucose |
| CN102459295A (en) * | 2009-04-07 | 2012-05-16 | 格礼卡姆股份公司 | Synthesis of 2'-o-fucosyllactose |
| JP2014224055A (en) * | 2013-05-15 | 2014-12-04 | 国立大学法人群馬大学 | Novel sugar donors and methods of synthesizing sugar chains using the same |
| WO2015036637A1 (en) * | 2013-09-13 | 2015-03-19 | Consejo Superior De Investigaciones Cientificas (Csic) | Method for the synthesis of kojibiose and the application thereof in the production of food and pharmaceutical compositions |
-
2018
- 2018-01-23 CN CN201810061764.XA patent/CN108084234A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996006102A1 (en) * | 1994-08-24 | 1996-02-29 | Ciba-Geigy Ag | Process for the preparation of oligosaccharide mixtures |
| CN102459295A (en) * | 2009-04-07 | 2012-05-16 | 格礼卡姆股份公司 | Synthesis of 2'-o-fucosyllactose |
| CN102212087A (en) * | 2011-01-24 | 2011-10-12 | 南京工业大学 | Method for preparing 3,6-branched triglucose |
| JP2014224055A (en) * | 2013-05-15 | 2014-12-04 | 国立大学法人群馬大学 | Novel sugar donors and methods of synthesizing sugar chains using the same |
| WO2015036637A1 (en) * | 2013-09-13 | 2015-03-19 | Consejo Superior De Investigaciones Cientificas (Csic) | Method for the synthesis of kojibiose and the application thereof in the production of food and pharmaceutical compositions |
Non-Patent Citations (2)
| Title |
|---|
| 孟歌: "《当代新药合成工艺》", 30 September 2015, 西安交通大学出版社 * |
| 崔建华等: "《基础化学》", 31 August 2014, 广西人民出版社 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109021036A (en) * | 2018-08-13 | 2018-12-18 | 佛山科学技术学院 | The method that α-connection disaccharides is combined to by the random glycosyl of unprotected monosaccharide |
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