Preparation method of 7beta,10beta-dimethoxy-10-deacetylbaccatin III
A technology of baccatin and dimethoxy, which is applied in the production of bulk chemicals and organic chemistry, can solve the problems of long steps and easy introduction of impurities, and achieve safe and reliable production
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Embodiment 1
[0037] Example 1: Synthesis of 7β, 13β-bis(triethylsilyl)-10-deacetylbaccatin III (compound II)
[0038] 10-DAB (50g, 92mmol) was dissolved in anhydrous pyridine (100ml), under the protection of nitrogen, triethylchlorosilane (40ml) was added at 0°C, raised to room temperature and reacted for 16h, and the temperature of the reaction mixture was raised to 110°C, Then add triethylchlorosilane (40ml), react at about 110°C for 2 hours, then lower the reaction mixture to room temperature, add water (300ml) to dilute, extract with methyl tert-butyl ether (100ml), and check the water layer by TLC No product. The organic layer was washed with 1 mol / L hydrochloric acid (100ml), washed with water (100ml×2), dried over sodium sulfate, filtered, concentrated under reduced pressure to about 1 / 10 of the original volume, added petroleum ether (40ml) to crystallize, and collected the white solid to obtain 28.6 g, yield: 40%.
[0039] 1 H-NMR (400MHz; deuterated chloroform): δ (ppm) 0.55 an...
Embodiment 2
[0040] Example 2: Synthesis of 13β-triethylsilyl-10-deacetylbaccatin III (compound III)
[0041] Dissolve 7β,13β-bis(triethylsilyl)-10-deacetylbaccatin III (10 g, 13 mol) in dichloromethane (100 ml) and add triethylamine hydrofluoride at room temperature (80ml), stirred at room temperature for 16h, TLC detected that the reaction of raw materials was complete, added water (100ml×3) to wash, washed with saturated sodium bicarbonate (100ml), washed with water (100ml), dried over sodium sulfate, filtered, concentrated under reduced pressure to the original The volume was about 1 / 10, petroleum ether (40ml) was added to crystallize, and the white solid was collected to obtain 6.5g, yield: 76%, content: 96%.
[0042] 1 H-NMR (400MHz; deuterated chloroform): δ (ppm) 0.63 ~ 0.70 (6H, m, CH 2 ethyl); 0.99~1.04 (9H, t, J=8.0, CH 3 ethyl); 1.09 (3H, s, CH 3 ); 1.16 (3H, s, CH 3 ); 1.45~1.47 (1H, d, J=7.6, OH 7); 1.60 (1H, s, OH 1); 1.74 (3H, s, CH 3 ); 1.79~1.86 and 2.55~2.63 (1H, 2...
Embodiment 3
[0043] Example 3: Synthesis of 13β-triethylsilyl-7β, 10β-dimethoxy-10-deacetylbaccatin III (Compound IV)
[0044] Dissolve 13β-triethylsilyl-10-deacetylbaccatin III (10g, 15.2mol) in tetrahydrofuran (20ml), add iodomethane (50ml), cool the reaction solution to 0°C, and Potassium tert-butoxide (5.1mg, 45.6mmol) was added under protection, and reacted at 0°C for about 1h after the addition. TLC detected that the reaction of the raw materials was complete, adding glacial acetic acid (2ml) to quench the reaction, and distilling under reduced pressure to remove tetrahydrofuran and methyl iodide. Dissolve the concentrated solution with isopropyl ether (40ml), wash with water (20ml), wash with saturated sodium bicarbonate (20ml), wash with water (20ml), dry over anhydrous sodium sulfate, filter, and concentrate under reduced pressure to obtain a crude product, which is directly for the next reaction.
[0045] 1 H-NMR (400MHz; deuterated dimethyl sulfoxide): δ (ppm) 0.63 ~ 0.74 (6H,...
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