Glucoside containing 1,2,3-triazole structure, preparation method and application
A technology of glucopyranoside and triazole, which is applied in the field of type 2 sodium glucose transporter inhibitor and its preparation, and can solve the problems of hepatotoxicity, weight and the like
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Embodiment 1
[0034] 4-Benzyl-1,2,3-triazol-1-yl β-D-glucopyranoside (I-1)
[0035]
[0036] A 100mL round bottom flask was added with 3.73g (10mmol) of compound II, 1.16g (10mmol) of compound III-1 and 30mL of absolute ethanol, and the reaction mixture was heated and refluxed for 12 hours under electromagnetic stirring, and cooled. The solvent was evaporated from the reaction mixture on a rotary evaporator, and the residue was purified by column chromatography to obtain the pure compound IV-1. The obtained compound IV-1 was dissolved in 100mL of absolute methanol with 0.10g (1.85mmol) of solid MeONa dissolved in advance, stirred at room temperature for 1 hour, then added 5.0g of dry 732 type strongly acidic cation exchange resin, stirred at room temperature 3 hours. The resin was removed by suction filtration, and the filtrate was evaporated to dryness to obtain a white solid, which was dried to obtain Compound I-1. Colorless crystals, 2.73g, yield 85%. ESI-MS, m / z=322 ([M+H] + ). ...
Embodiment 2
[0039] 4-[(2-Chlorophenyl)methyl]-5-methyl-1,2,3-triazol-1-yl β-D-glucopyranoside (I-2)
[0040]
[0041]A 100mL round bottom flask was added with 3.73g (10mmol) of compound II, 1.65g (10mmol) of compound III-2 and 30mL of absolute ethanol, and the reaction mixture was heated to reflux for 12 hours under electromagnetic stirring and cooled. The solvent was evaporated from the reaction mixture on a rotary evaporator, and the residue was purified by column chromatography to obtain the pure compound IV-2. The obtained compound IV-2 was dissolved in 100mL of absolute methanol with 0.10g (1.85mmol) of solid MeONa dissolved in advance, stirred at room temperature for 1 hour, then added 5.0g of dry 732 type strongly acidic cation exchange resin, stirred at room temperature 3 hours. The resin was removed by suction filtration, and the filtrate was evaporated to dryness to obtain a white solid, which was dried to obtain compound I-2. Colorless crystals, 3.18g, yield 86%. ESI-MS, ...
Embodiment 3
[0044] 4-[(4-Ethylphenyl)methyl]-5-methyl-1,2,3-triazol-1-yl β-D-glucopyranoside (I-3)
[0045]
[0046] A 100mL round bottom flask was added with 3.73g (10mmol) of compound II, 1.58g (10mmol) of compound III-3 and 30mL of absolute ethanol, and the reaction mixture was heated and refluxed for 12 hours under electromagnetic stirring, and cooled. The solvent was evaporated from the reaction mixture on a rotary evaporator, and the residue was purified by column chromatography to obtain the pure compound IV-3. The obtained compound IV-3 was dissolved in 100mL of anhydrous methanol with 0.10g (1.85mmol) of solid MeONa dissolved in advance, stirred at room temperature for 1 hour, then added 5.0g of dry 732 type strongly acidic cation exchange resin, stirred at room temperature 3 hours. The resin was removed by suction filtration, and the filtrate was evaporated to dryness to obtain a white solid, which was dried to obtain compound I-3. Colorless crystals, 2.94g, yield 81%. ESI...
PUM
Login to View More Abstract
Description
Claims
Application Information
Login to View More