A kind of preparation method and application of whole acyl-protected 1-glucosinolate, glucose 1-thiol
A technology of glucosinolate and glucose, which is applied in the fields of medicine and sugar chemical synthesis, can solve the problems of inability to carry out the reaction, small solubility, and no effect, and achieve high reaction efficiency and yield, no irritation and odor, and mild conditions Effect
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Embodiment 1
[0043] Weigh 1,2,3,4,6-penta-O-acetyl-D-glucose (1g, 2.6mmol) and dissolve it in ethyl acetate (15mL), add potassium thioacetate (590mg, 5.2mmol), Stir and mix, add boron trifluoride diethyl ether (1.3mL, 10.4mmol), react at a constant temperature of 50°C for 4 hours, cool the reaction solution to room temperature, add triethylamine dropwise to neutralize to pH = 7, concentrate under reduced pressure and column Chromatography yielded 987 mg of 2,3,4,6-tetra-O-acetyl-1-S-acetyl-β-D-glucose with a yield of 95%. 1 H NMR (400MHz, CDCl 3 ): δ5.29-5.24(2H,m,H-3,H-1),5.15-5.08(2H,m,H-2,H-4),4.26(1H,dd,J=12.4Hz,J =4.4Hz, H-6a), 4.09(1H, dd, J=12.4Hz, J=2.0Hz, H-6b), 3.83(1H, ddd, J=10.0Hz, J=4.4Hz, J=2.0Hz ,H-5),2.38(3H,s,SCOCH 3 ),2.07,2.03,2.02,2.00(12H,4×s,COCH 3 ).
Embodiment 2
[0045] Under traditional one-step conditions, direct use of potassium thioacetate leads to extremely low yields:
[0046] Weigh 1,2,3,4,6-penta-O-acetyl-D-glucose (1g, 2.6mmol) and dissolve it in dichloromethane (15mL), add potassium thioacetate (590mg, 5.2mmol), Stir and mix, add boron trifluoride diethyl ether (578 μL, 5.2 mmol), react at room temperature for 24 hours, dropwise add triethylamine to neutralize to pH = 7, concentrate under reduced pressure and column chromatography to obtain 2,3,4,6-tetra -O-acetyl-1-S-acetyl-β-D-glucose 312 mg, yield 30%.
Embodiment 3
[0048] Under the traditional one-step process conditions, the use of potassium thioacetate while using dimethylformamide as a solvent causes the raw materials to not react:
[0049] Weigh 1,2,3,4,6-penta-O-acetyl-D-glucose (1g, 2.6mmol) and dissolve it in dimethylformamide (15mL), add potassium thioacetate (590mg, 5.2mmol ), stirring and mixing, adding boron trifluoride diethyl ether (578 μL, 5.2 mmol), and reacting at a constant temperature of 50° C. for 4 hours, the raw materials did not react, and the yield was 0.
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