alpha-D-Glucopyranosyl bromide, tetraacetate → 4-[(4-Isopropoxy-phenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-o-acetyl-beta-d-glucopyranosyloxy)-1h-pyrazole

Participants

Reaction Conditions

Reaction Steps

To a suspension of 4-[(4-isopropoxyphenyl)methyl]-5-methyl-1,2-dihydro-3H-pyrazol-3-one (46 mg), acetobromo-α-D-glucose (99 mg) and 4A molecular sieves in tetrahydrofuran (3 mL) was added silver carbonate (66 mg), and the mixture was stirred at 65° C. overnight under light shielding. The reaction mixture was purified by column chromatography on aminopropyl silica gel (eluent: tetrahydrofuran), and successively by preparative thin layer chromatography on silica gel (developing solvent: ethyl acetate/hexane=2/1) to give 4-[(4-isopropoxyphenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (42 mg).

Provenance & Evidence