Nonionic surfactants. Regioselective synthesis of fatty acid esters of alpha- and beta-glucopyranose

被引：5

作者：

DeLuca, D ^{[1
]}

DeNino, A ^{[1
]}

Liguori, A ^{[1
]}

Procopio, A ^{[1
]}

Sindona, G ^{[1
]}

机构：

[1] UNIV CALABRIA,DIPARTIMENTO CHIM,I-87030 ARCAVACATA,CS,ITALY

来源：

LIPIDS | 1997年 / 32卷 / 05期

关键词：

D O I：

10.1007/s11745-997-0071-7

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Lipophilic esters of saccharides belong to the family of nonionic surfactants widely employed in pharmaceutical and cosmetics formulations. A very simple method is presented whereby 6-O-esters of alpha- and beta-glucose can be prepared and isolated. Good results have been obtained in the synthesis of 6-O-oleyl derivatives by simple acylation with appropriate oleyl chloride. She condensing agent bis(2-oxo-3-oxazolidinyl) phosphinic chloride (BOP-CI) allows the preparations of the same esters with better regioselectivity but with yields strongly dependent on the aliphatic chain length of the carboxylic acids employed.

引用

页码：559 / 563

页数：5

共 38 条

[1] ENZYME CATALYZED PREPARATION OF 6-O-ACYLGLUCOPYRANOSIDES [J].

ADELHORST, K ;

BJORKLING, F ;

GODTFREDSEN, SE ;

KIRK, O .

SYNTHESIS-STUTTGART, 1990, (02) :112-115

[2]

AHEMED S, 1987, J CHEM SOC CHEM COMM, P114

[3]

Andree H., 1991, TENSIDE SURFACT DET, V28, P413

[4]

Attwood D., 1983, SURFACTANT SYSTEMS

[5] SUGAR CHEMISTRY WITHOUT PROTECTING GROUPS-III - A FACILE CHEMICAL SYNTHESIS OF 6-O-ACYL-D-GLYCOPYRANOSES AND METHYL-6-O-ACYL-D-GLYCOPYRANOSIDES [J].

BACZKO, K ;

PLUSQUELLEC, D .

TETRAHEDRON, 1991, 47 (23) :3817-3828

[6] SELECTIVE MODIFICATION OF UNPROTECTED MONOSACCHARIDES AND DISACCHARIDES VIA ESTER AND ETHER BONDS [J].

BERAUD, P ;

BOURHIM, A ;

CZERNECKI, S ;

KRAUSZ, P .

TETRAHEDRON LETTERS, 1989, 30 (03) :325-326

[7]

BOTTLE S, 1984, J CHEM SOC CHEM COMM, P385, DOI 10.1039/c39840000385

[8] 2 NEW PROTECTED ACYL PROTECTING GROUPS FOR ALCOHOLIC HYDROXY FUNCTIONS [J].

BROWN, JM ;

CHRISTODOULOU, C ;

REESE, CB ;

SINDONA, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (08) :1785-1790

[9]

BUSH P, 1994, AGROFOOD IND HI TECH, P23

[10] ENZYMATIC-SYNTHESIS OF VARIOUS 1'-O-SUCROSE AND 1-O-FRUCTOSE ESTERS [J].

CARREA, G ;

RIVA, S ;

SECUNDO, F ;

DANIELI, B .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (05) :1057-1061

← 1 2 3 4 →