C-glycoside and C-glycoside compound containing substituted aromatic rings as well as preparation and use thereofb
A technology of compound and sugar carbon glycosides, which is applied in the field of medicine, can solve the problem of nerve damage without therapeutic effect
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Embodiment 1
[0029] Example 1: (3',4',5'-trimethoxyphenyl)methyl-1-thio-β-D-glucopyranoside (S01)
[0030] A: (3′,4′,5′-trimethoxyphenyl)methyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside
[0031] 1.31g (5mmol) 1-bromomethyl-3,4,5-trimethoxybenzene and 1.82g (5mmol) 2,3,4,6-tetra-O-acetyl-β-D-1-sulfur Dissolve glucopyranose in 30mL of acetone, add 0.69g (5mmol) of anhydrous potassium carbonate, and heat to reflux for 6h. After cooling, filter, wash the solid with acetone, and concentrate the filtrate to remove the solvent to obtain 2.70 g of syrup, and the yield of the crude product is 99.2%. R f =0.25, petroleum ether (60-90°C):ethyl acetate=2:1.
[0032] B: (3′,4′,5′-trimethoxyphenyl)methyl-1-thio-β-D-glucopyranoside (S01)
[0033] 2.70g (4.96mmol) of (3',4',5'-trimethoxyphenyl)methyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D- Glucopyranoside was dissolved in 30 mL of methanol, 4.14 g (30 mmol) of anhydrous potassium carbonate was added, and the reaction was stirred at room temperatur...
Embodiment 2
[0034] Example 2: (4'-methylphenyl)methyl-1-thio-β-D-glucopyranoside (S02)
[0035] A: (4′-methylphenyl)methyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside
reference example 1
[0036] Reference Example 1 Step A reaction synthesis, to obtain 2.20g syrup, crude product yield 94.0%. R f =0.71, petroleum ether (60-90°C):ethyl acetate=2:1.
[0037] B: (4′-methylphenyl)methyl-1-thio-β-D-glucopyranoside (S02)
[0038] Reference Example 1 Step B reaction synthesis, prepared 1.17g syrup, yield 83.0%. 1 HNMR (CD 3 OD) δ (ppm): 2.29 (3H, s, -CH 3 ), 3.17-3.31 (4H, H-5, H-4, H-3, H-2), 3.65 (1H, dd, H-6a, J 1 =6.2Hz,J 2 = 12.2Hz), 3.79 (1H, d, -CHPh', J = 13.2Hz), 3.88 (1H, dd, H-6b, J 1 =2.2Hz,J 2= 12.2Hz), 3.99 (1H, d, -CHPh', J = 13Hz), 4.13 (1H, d, H-1, J = 9.6Hz), 7.10 (2H, d, Ph', J = 7.8Hz) , 7.22 (2H, d, Ph', J = 8.1 Hz). -c ESI m / z: 299(M-1), 359(M+Na+2H 2 O), 599(2M-1).
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