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With boron trifluoride diethyl etherate; In dichloromethane; at -20 - 15℃; for 4h;Inert atmosphere; Molecular sieve;
General procedure: Powdered 4 A molecular sieves (5.02 g) were added to a solution of ethyl 4-hydroxybenzoate 4a (0.91 g, 5.00 mmol) and methyl 2,3,4-tri-O-acetyl-1-O-trichloroacetylimidoyl-alpha-d-glucopyranuronate 8 (3.35 g, 7.00 mmol) in dry DCM (20 mL). The mixture was cooled to -20 C and BF3·Et2O (0.246 mL, 2.00 mmol) was added dropwise. The mixture was allowed to warm gradually to 15 C under continued stirring for 4 h. The reaction was quenched with triethylamine and the mixture was then filtered through a pad of Celite and concentrated. The residue was purified by column chromatography (Silica gel, Pet ether/EtOAc 3:1 to 2.5: 2) giving rise to the glucuronide conjugate as an off-white solid (2.20 g, 92%).
With boron trifluoride diethyl etherate; In dichloromethane; at -20 - 15℃; for 4h;Inert atmosphere; Molecular sieve;
General procedure: Powdered 4 A molecular sieves (5.02 g) were added to a solution of ethyl 4-hydroxybenzoate 4a (0.91 g, 5.00 mmol) and methyl 2,3,4-tri-O-acetyl-1-O-trichloroacetylimidoyl-alpha-d-glucopyranuronate 8 (3.35 g, 7.00 mmol) in dry DCM (20 mL). The mixture was cooled to -20 C and BF3·Et2O (0.246 mL, 2.00 mmol) was added dropwise. The mixture was allowed to warm gradually to 15 C under continued stirring for 4 h. The reaction was quenched with triethylamine and the mixture was then filtered through a pad of Celite and concentrated. The residue was purified by column chromatography (Silica gel, Pet ether/EtOAc 3:1 to 2.5: 2) giving rise to the glucuronide conjugate as an off-white solid (2.20 g, 92%).
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