Oligosaccharide synthesizing method

A synthesis method and oligosaccharide technology, applied in chemical instruments and methods, sugar derivatives, sugar derivatives, etc., can solve the problems of expensive catalysts, easy to pollute the environment, and low synthesis efficiency, and achieve cheap and easy-to-obtain catalysts, shorten The effect of simple reaction route and donor structure

Active Publication Date: 2017-05-17
EAST CHINA NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Although the above-mentioned disclosed technology can activate propargyl alcohol glycoside donors and glycosyl acceptors to synthesize oligosaccharides, the disadvantages are: (1) using AuCl 3 , AgSbF 6 , AgOTf and other precious metal catalysts are expensive, not easy to obtain, high production cost, and not suitable for industrial production; (2) the acceptor used can only be the glycosyl acceptor whose 6-position is a hydroxyl group, and the acceptor generally needs to go through the previous step The glycosyl intermediate can only be obtained by removing its 6-Tr (trityl) protecting group, which leads to long reaction steps and low efficiency for the synthesis of oligosaccharides by the above method
(3) Au in the above method 3+ 、Ag + and other heavy metal ions are also easy to pollute the environment, which does not meet the requirements of green chemical development
[0012] The existing technology activates the propargyl alcohol glycoside donor to synthesize oligosaccharides, the catalyst is expensive, the production cost is high, the reaction steps are long, the synthesis efficiency is low, and the catalyst is easy to cause heavy metal ion environmental pollution, which is not suitable for large-scale production, which greatly limits the production of propargyl alcohol. Application of Alcohol Glycoside Donors in Oligosaccharide Synthesis

Method used

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  • Oligosaccharide synthesizing method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] The present invention carries out the synthesis of oligosaccharide (3a) according to the following reaction equation:

[0021]

[0022] Among them: 1a is full benzyl protected galactosyl propargyl glycoside; 2a is 2,3,4-tri-O-benzoyl-6-O-trityl-α-D-glucoside; 3a is 2,3,4-Tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzyl-D-galactosyl)-α-D-glucoside.

[0023] in N 2 Under protection, dry 29 mg (0.05 mmol) of all benzyl protected galactosyl propargyl glycosides with 37.5 mg (0.05 mmol) of 2,3,4-tri-O-benzoyl-6-O-trityl -α-D-glucoside was dissolved in 3ml of dichloromethane solvent, and 1.5mg of FeCl was added rapidly 3 ·6H 2 O into the reaction system, heated to 40°C for glycosylation reaction for 25 hours, TLC monitoring of the reaction process, after the completion of the reaction, add 200-300 mesh silica gel to the reaction solution, rotary evaporation, concentration to remove the solvent, and then separated by column chromatography , 45 mg of the product was oligosaccha...

Embodiment 2

[0027] The present invention carries out the synthesis of oligosaccharide (3b) according to the following reaction equation:

[0028]

[0029] Among them: 1b is the whole benzyl protected glucose propargyl glycoside; 2b is 2,3,4-tri-O-benzoyl-6-hydroxy-α-D-glucoside; 3b is 2,3,4- Tris-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzyl-D-glucosyl)-α-D-glucoside.

[0030] in N 2 Under protection, 0.06 mmol (35 mg) of dry whole benzyl-protected glucopropargyl glycoside and 0.05 mmol (25 mg) 2,3,4-tri-O-benzoyl-6-hydroxy-α-D-glucose methyl Glycosides and 1mg FeCl 3 Be dissolved in 3ml of acetonitrile solvent, be heated to 80 ℃ and carry out glycosylation reaction 15 hours, TLC monitors the reaction process, after the reaction is completed, reaction solution is by silica gel column chromatography (petroleum ether / ethyl acetate = 10:1) separation and purification, the product 43mg was oligosaccharide (3b), and its yield was 83%.

[0031] The product obtained above was analyzed and confirm...

Embodiment 3

[0034] The present invention carries out the synthesis of oligosaccharide (3b) according to the following reaction equation:

[0035]

[0036] in N 2 Under protection, dry 0.1 mmol (58 mg) of whole benzyl protected glucosyl propargyl glycoside and 0.05 mmol (25 mg) of 2,3,4-tri-O-benzoyl-6-hydroxy-α-D-glucose methyl Glycosides and 10mg FeCl 3 / C(FeCl 3 The mass ratio to activated carbon is 1:1) dissolved in 1.5ml tetrahydrofuran solvent, heated to 80°C for glycosylation reaction for 8 hours, TLC to monitor the reaction progress, after the reaction was completed, the reaction solution was rotary evaporated, concentrated to remove the solvent, and passed through the silica gel column After separation and purification by chromatography (petroleum ether / ethyl acetate=10:1), 40 mg of the product was obtained as oligosaccharide (3b), and the yield was 75%.

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Abstract

The invention discloses an oligosaccharide synthesizing method which is characterized in that full-benzyl protection propargyl alcohol glycoside is utilized as a glycosyl donor, 6-site glycosyl intermediate or glycosyl with a -Tr protecting group is utilized as a glycosyl acceptor, and the glycosyl donor and the glycosyl acceptor are dissolved in an organic solvent according to a mole ratio of (1 to 6mmol) to 1mmol to (0.1 to 1mmol) to perform glycosylation reaction under the catalysis of ferric salt. Compared with the prior art, the oligosaccharide synthesizing method achieves the purpose that the glycosyl donor directly perform glycosylation reaction with the 6-site glycosyl intermediate with the -Tr protecting group, oligosaccharide is synthesized through a one-pot method in high yield, a reaction route is shortened, operation steps are simplified, production cost is reduced, and heavy metal ion pollution is effectively avoided. In addition, the oligosaccharide synthesizing method has the advantages of being green, environment-friendly and suitable for industrial production and having larger technological innovation and good application prospect.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing oligosaccharides. Background technique [0002] The propargyl alcohol glycoside donor has the advantages of simple structure, convenient preparation and easy storage, and is an important glycosyl donor, which is gradually applied in sugar chemistry. At present, the preparation method of such glycosyl donors mainly uses gold, silver and other noble metal salts as catalysts for activating propargyl alcohol glycoside donors, and catalyzes their reaction with glycosyl acceptors to synthesize oligosaccharides. [0003] Public technology (1): S.Hotha and S.Kashyap, J.Am.Chem.Soc., 2006, 128, 9620-9621. The reaction equation is as follows: [0004] [0005] Public technology (2): S.K.Mamidyala and M.G.Finn, J.Org.Chem., 2009, 74, 8417-8420. The reaction equation is as follows: [0006] [0007] Public technology (3): A.K.Kayastha and S.Hotha, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/18C07H1/00
Inventor 张剑波孙国圣武玥刘安琪郭红
Owner EAST CHINA NORMAL UNIV
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