Efficient syntheses of bolaform surfactants from L-rhamnose and/or 3-(4-hydroxyphenyl)propionic acid

被引:14
|
作者
Akong, Firmin Obounou [1 ]
Bouquillon, Sandrine [1 ]
机构
[1] Univ Reims, UMR CNRS 7312, Inst Chim Mol Reims, F-51687 Reims 2, France
关键词
LIPASE-CATALYZED ESTERIFICATION; OLEFIN CROSS-METATHESIS; ORGANIC-SOLVENT MEDIA; ENZYMATIC-SYNTHESIS; PHENOLIC-ACIDS; NONCONVENTIONAL MEDIA; MICROBIAL-PRODUCTION; FATTY-ACIDS; D-XYLOSE; ESTERS;
D O I
10.1039/c5gc00448a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The efficient syntheses of new symmetric and asymmetric bolaamphiphiles derived from L-rhamnose and/or 3-(4-hydroxyphenyl)propionic acid are described. The bolaamphiphiles are obtained with good to high yields through a two-step reaction sequence involving, successively, a glycosylation (or an esterification) and a metathesis. The glycosylation was performed without solvent because the alcohols could be the solvent in this reaction. For the esterification, enzymatic catalysis was used which gave esters with high yields which increased with the carbon chain length. Finally, the metathesis step was performed in the presence of a Grubbs' I catalyst without protection steps in only dichloromethane without the addition of methanol.
引用
收藏
页码:3290 / 3300
页数:11
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