Synthetic method for 3,6-site branched glucohexaose

A synthesis method and glucose technology, applied in the field of synthesis of 3,6-position branched hexaglucan, can solve the problems of unfavorable industrial production, complex synthesis method, low utilization rate of raw materials, etc., and achieve convenient operation, simple synthesis route, The effect of high utilization rate of raw materials

Active Publication Date: 2018-11-27
江西艾立斯特生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The synthesis methods of oligosaccharide activators reported so far are relatively complicated, and the utilization

Method used

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  • Synthetic method for 3,6-site branched glucohexaose
  • Synthetic method for 3,6-site branched glucohexaose
  • Synthetic method for 3,6-site branched glucohexaose

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Preparation of glucotriose donor:

[0021] 1) Dissolve 3.705g, 5mmol of benzoylglucose trichloroacetimidate in 30mL of dichloromethane to obtain solution A, and dissolve 0.735g, 2.5mmol of tert-butyldimethylsilyl-α-D-glucopyranose Dissolve in 15mL of dichloromethane to obtain solution B, mix B and A to obtain solution C, add 230μL, 2mmol of TMSOTf catalyst to C, and then add Molecular sieves, after reacting at 25°C for 4 hours, thin-layer chromatography analysis showed that the reaction was complete, filtered with suction, evaporated the solvent under reduced pressure, separated by column chromatography, and used ethyl acetate / cyclohexane (1 / 3) as eluent Rinse and collect the corresponding components to obtain pure trisaccharides with a yield of 91.3%;

[0022] 2) Dissolve 7.250g, 5mmol trisaccharide in 30mL DMF, heat to 70°C to completely dissolve the glucose, add 2.9mL, 3.5mmol pyridine, take out the flask and cool it to 25°C, place the flask in an ice bath, add dro...

Embodiment 2

[0028] Preparation of Glucotriose Acceptor

[0029] 1) Dissolve 1.481g, 2mmol of benzoylglucose trichloroacetimidate in 10mL of dichloromethane to obtain solution a, and dissolve 0.588g, 2mmol of tert-butyldimethylsilyl-α-D-glucopyranose In 10mL of dichloromethane, to obtain solution b, 1.241g, 2mmol of 4,6-benzylidene-2,3-di-O-benzoylglucose trichloroacetimidate was dissolved in 10mL of dichloromethane, To obtain solution c, mix solution a, solution b, and solution c to obtain solution d, add 80 μ L, 0.70 mmol TMSOTf catalyst to solution d, add Molecular sieves, after reacting at 25°C for 3 hours, thin-layer chromatography analysis showed that the reaction was complete, filtered with suction, evaporated the solvent under reduced pressure, separated by column chromatography, and used ethyl acetate / cyclohexane (1 / 3) as eluent Rinse and collect the corresponding components to obtain pure trisaccharides with a yield of 89.7%.

[0030] 2) 1.330g, 1mmol trisaccharides were disso...

Embodiment 3

[0034] Synthesis of target compounds

[0035] 1) 3.377g, 2mmol triglucose donor, 2.484g, 2mmol triglucose acceptor and Molecular sieves were dissolved in 40mL of anhydrous dichloromethane, stirred for 50min under the protection of nitrogen, then 50μL, 0.44mmol TMSOTf catalyst was added dropwise, and reacted at 25°C for 4h. Thin-layer chromatography analysis showed that the reaction was complete, suction filtered, and evaporated under reduced pressure The solvent was separated by column chromatography, washed with ethyl acetate / cyclohexane (1 / 2) as eluent, and the corresponding components were collected to obtain pure hexasaccharide with a yield of 81.9%.

[0036] 2) Dissolve 5.536g, 2mmol hexasaccharide in 25mL, 1% hydrochloric acid-methanol solution, react at 25°C for 1-2h, thin-layer chromatography analysis shows that the reaction is complete, evaporate the solvent under reduced pressure, and separate by column chromatography, Ethyl acetate / cyclohexane (1 / 2) was used as th...

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Abstract

The invention discloses a synthetic method for 3,6-site branched glucohexaose and belongs to the technical field of natural product synthesis. The synthetic method comprises the following steps: coupling trichloroacetimidate of glucose as a glycosyl donor with tertiary butyl dimethyl silicon-alpha-D-glucopyranose as a glycosyl acceptor to generate trisaccharide; carrying out benzoyl protection andacid hydrolysis to remove end position protecting groups; then carrying out activation to obtain a glucotriose donor; coupling trichloroacetimidate of glucose and 4,6-benzylidenyl-2,3-di-O-benzoyl trichloroacetimidate of glucose as a glycosyl donor with tertiary butyl dimethyl silicon-alpha-D-glucopyranose as a glycosyl acceptor to synthesize trisaccharide; carrying out hydrolysis to remove 4,6-benzylidenyl to obtain the glucotriose acceptor; coupling the trisaccharide donor with the trisaccharide acceptor to obtain hexaose; and then carrying out de-protection to obtain the targeted 3,6-sitebranched glucohexaose. The synthetic method provided by the invention is concise in synthetic route and convenient to operate. In the whole process, the utilization ratio of raw materials is high, andthe method is an efficient synthetic method.

Description

technical field [0001] The invention belongs to the technical field of natural product synthesis, and in particular relates to a synthesis method of 3,6-position branched hexaglucan. Background technique [0002] The main chain of glucose oligosaccharide is 1→6β linkage, and the side chain is 1→3β linkage. American scientists obtained it from the polysaccharide of the mycelium cell wall of the fungus Phyto-phthora megasperma f.Sp.Glycinea (Phytophthora soybean) in the 1980s. Glucose oligosaccharides are very important elicitors in plants, which can efficiently induce plant disease resistance. Oligosaccharides activate the plant immune system and cause plants to produce a series of defense responses to resist external aggression. Its role is produced through the following pathways: oligosaccharides recognize plant receptors and generate defense signals, activate intracellular signal transduction pathways and amplify, Thereby activating and expressing the genes related to th...

Claims

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Application Information

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IPC IPC(8): C08B37/02
CPCC08B37/0009
Inventor 朱玉亮
Owner 江西艾立斯特生物科技有限公司
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