Decanol glucose dimeric surfactant and preparation method thereof
A gemini surface, glucose technology, applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., can solve the problem that sugar-based gemini surfactants are difficult to meet the needs of the market, and achieve good solubilization effect, Simple preparation method
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Embodiment 1
[0028] Weigh 295.6mg (0.6mmol) of tetraacetylglucose trichloroacetimidate, use 5ml of anhydrous dichloromethane as solvent, add 98.08mg (0.2mmol) of decanol double chain, cool and stir for 15min, then add catalytic amount of trifluoro Boronium diethyl ether (the molar weight is 5% of the molar weight of the decanol duplex chain), the reaction process is monitored by thin-layer chromatography, and after the reaction is completed, it is extracted, dried and rotary evaporated, and the column chromatography (eluent is sherwood oil: ethyl acetate) ester = 3:1) and collected into a round bottom flask, then rotary evaporated to obtain a light yellow liquid.
[0029] Take 115.1 mg (0.1 mmol) of the product obtained in the previous step reaction and use 20 ml of anhydrous methanol (excessive methanol added, in order to buffer the pH value of the alkali process during the purpose, to avoid side reactions caused by excessive local pH value) as a solvent, add 10.8 mg of sodium methoxide (...
Embodiment 2
[0038] Weigh 295.6mg (0.6mmol) of tetraacetylglucose trichloroacetimidate, use 5ml of anhydrous dichloromethane as solvent, add 98.08mg (0.2mmol) of decanol double chain, cool and stir for 15min, then add catalytic amount of trifluoro Trimethylsilicone methanesulfonate (the molar weight is 5% of the molar weight of the decyl alcohol duplex chain), after the reaction is completed, it is extracted, dried and rotary evaporated, purified by column chromatography, collected into a round bottom flask and then rotary evaporated The light yellow liquid obtained is decyl alcohol glucose gemini surfactant.
[0039]Take 115.1 (0.1 mmol) of the product obtained in the previous step reaction and use 20 ml of anhydrous methanol as a solvent, add 10.8 mg of sodium methoxide (0.2 mmol), filter and rotary evaporate after the reaction, and obtain 78.9 mg (0.0967 mmol) of a colorless syrupy liquid. Yield 48%.
[0040] The structural identification and surface activity test data of the decyl alc...
Embodiment 3
[0042] Weigh 589.2mg (1.2mmol) of tetraacetylglucose trichloroacetimidate, use 5ml of anhydrous dichloromethane as solvent, add 98.08mg (0.2mmol) of decanol double chain, cool and stir for 15min, then add catalytic amount of trifluoro Trimethylsilicone methanesulfonate (the molar weight is 5% of the molar weight of the decyl alcohol duplex chain), after the reaction is completed, it is extracted, dried and rotary evaporated, purified by column chromatography, collected into a round bottom flask and then rotary evaporated A pale yellow liquid was obtained.
[0043] Take 117.0mg (0.1mmol) of the product obtained in the previous step reaction, use 20ml of anhydrous methanol as a solvent, add 5.0mg of sodium hydride (0.2mmol), after the reaction is completed, filter and rotary evaporate to obtain a colorless syrupy liquid. Active agent 75.3 mg (0.0923 mmol), yield 46%.
[0044] The structural identification and surface activity test data of the decyl alcohol glucose gemini surfac...
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