摘要
A series of novel coumarin glycoside esters(1-9) was synthesized through the acylation reaction of 4-methylcoumarin-7-O-β-D-glucoside(11) with different long chain fatty acids catalyzed by lipase in organic medium. The acylation occurred regioselectively at the 6'-OH of glycosyl moiety. The enzymatic synthesis was optimized to achieve 54%-70% yield using immobilized lipase(Novozym 435, 10 mg/mL) as catalyst and acetone and pyri- dine(9:1, volume ratio, water content〈1%) as solvent with an acyl donor/coumarin glycoside molar ratio of 10:1 at a temperature of 40--50 ℃ for 96 h. All the synthesized compounds were confirmed.
A series of novel coumarin glycoside esters(1-9) was synthesized through the acylation reaction of 4-methylcoumarin-7-O-β-D-glucoside(11) with different long chain fatty acids catalyzed by lipase in organic medium. The acylation occurred regioselectively at the 6'-OH of glycosyl moiety. The enzymatic synthesis was optimized to achieve 54%-70% yield using immobilized lipase(Novozym 435, 10 mg/mL) as catalyst and acetone and pyri- dine(9:1, volume ratio, water content〈1%) as solvent with an acyl donor/coumarin glycoside molar ratio of 10:1 at a temperature of 40--50 ℃ for 96 h. All the synthesized compounds were confirmed.
基金
Supported by the National Natural Science Foundation of China(Nos.21342015, J1210040) and the Hunan Provincial Natu- ral Science Foundation, China(No. 14JJ2048).