Synthesis of a Lipid Derivative Containing Sialic Acid Group and Its Application in Pharmaceutical Preparations
A technology of lipid derivatives and sialic acid, which is applied in the field of preparation and modification of microparticle preparations, and can solve the problems of high difficulty and many synthesis steps.
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Embodiment 1
[0103] Example 1 Synthesis of Neu5Ac-AE
[0104] Weigh Neu5Ac (1.55g, 5mmol), put it in a 100mL eggplant-shaped flask, add 40mL DMF, heat to dissolve, add 4-PPY (0.74g, 5mmol), then add 1mLTEA, and stir in a water bath at 60°C for 6h. Transfer the reaction solution to a 10mLEP tube, centrifuge at 2000rpm for 5min, pour off the supernatant, wash 3 times with anhydrous diethyl ether, N 2 After blowing dry, vacuum-dried to obtain a white powdery solid, namely Neu5Ac-4PPY. Weigh Neu5Ac-4PPY activated ester (439mg, 1mmol) and dissolve it in 15mL DMF, heat to 60°C, vacuumize, and fill with N 2 . Another weighed AE (232mg, 3mmol) was added to the Neu5Ac-4-PPY activated ester system, vacuumed and filled with N 2 , the reaction was stirred in a water bath at 60°C, and the reaction was stopped after 1 hour. First, the tiny insoluble substances in the reaction liquid system were filtered out with a 0.45 μm organic membrane to obtain a clear reaction liquid. The reaction system / anhydro...
Embodiment 2
[0112] Example 2 Synthesis of Neu5Ac-AP
[0113] Weigh Neu5Ac (1.55g, 5mmol), put it in a 100mL eggplant-shaped bottle, add 40mL DMF and a stirrer, heat to dissolve, add 4-PPY (0.74g, 5mmol), then add 1mL TEA, and stir in a water bath at 60°C for 6h . The reaction solution was transferred to 2000rpm and centrifuged for 5min, the supernatant was poured off, washed 3 times with anhydrous diethyl ether, N 2 After drying, vacuum-dry to obtain a white powdery solid, namely Neu5Ac-4PPY. Weigh Neu5Ac-4PPY activated ester (439mg, 1mmol) and dissolve it in 15mL DMF, heat to 60°C, vacuumize, and fill with N 2 . Another AP (273mg, 3mmol) was weighed and added to the Neu5Ac-4PPY activated ester system, vacuumed and filled with N 2 , the reaction was stirred in a water bath at 60°C, and the reaction was stopped after 1h. First, the tiny insoluble substances in the reaction liquid system were filtered out with a 0.45 μm organic membrane to obtain a clear reaction liquid. The reaction syst...
Embodiment 3
[0116] Synthesis of Example 3 AC-CH
[0117] Weigh CH (386 mg, 1 mmol) into an eggplant-shaped bottle, add DCM to dissolve it, add 417 μL of TEA, vacuumize, and fill with N 2 , stirred in an ice-water bath for 20 min, measured AC (245 μL, 3 mmol) and added dropwise the DCM solution of AC in an eggplant-shaped bottle under ice-water bath conditions, extracted the air in the reaction system, and filled it with N 2 , stirred in an ice-water bath for 1 h, and reacted at room temperature for 24 h. The DCM was removed by spinning in vacuo. Transfer it to a beaker with water, transfer it to a 10mLEP tube, centrifuge at 2000rpm to discard the supernatant, and freeze-dry the lower layer of pale yellow precipitate to obtain the product AC-CH.
[0118] The structure is shown in the following formula:
[0119]
[0120] Mass Spectrum: m / z 463.3561, AC-CH+ 23 Na peak, indicating the successful synthesis of AC-CH. Spectrum see attached image 3 .
[0121] Infrared: The hydroxyl str...
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