CARBOHYDRATE PROTEIN INTERACTIONS - SYNTHESES OF AGGLUTINATION INHIBITORS OF WHEAT-GERM-AGGLUTININ BY PHASE-TRANSFER CATALYSIS

被引：51

作者：

ROY, R

TROPPER, FD

机构：

来源：

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1991年 / 69卷 / 05期

关键词：

PHASE TRANSFER CATALYSIS; ARYL; 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDES;

D O I：

10.1139/v91-121

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Starting from chloride 1, a series of para-substituted aryl 2-acetamido-2-deoxy-beta-D-glucopyranosides were prepared using phase transfer catalysis conditions with tetrabutylammonium hydrogen sulfate in 1 M sodium hydroxide and methylene chloride at room temperature. Zemplen de-O-acetylation afforded the unprotected glycosides. Optimization of reaction conditions was evaluated. Several functional group manipulations were effected to widen the number and nature of the para-substituents.

引用

页码：817 / 821

页数：5

共 24 条

[1]

BOGUSIAK J, 1985, POL J CHEM, V59, P293

[2]

BREWSTER K, 1979, TETRAHEDRON LETT, P5051

[3] ADVANCES IN PHASE-TRANSFER CATALYSIS [J].

DEHMLOW, EV .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1977, 16 (08) :493-505

[4]

DESS D, 1981, SYNTHESIS-STUTTGART, P883

[5]

GOLDSTEIN IJ, 1986, LECTINS PROPERTIES F, P209

[6] PHASE TRANSFER CATALYSIS - EVALUATION OF CATALYSTS [J].

HERRIOTT, AW ;

PICKER, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (09) :2345-2349

[7]

Horton D., 1972, METHODS CARBOHYDR CH, V6, P282

[8]

JONES CS, 1980, J BIOL CHEM, V255, P1861

[9]

KUNZ H, 1989, LIEBIGS ANN CHEM, P45

[10]

LEEBACK DH, 1963, BIOCH PREP, V10, P118

← 1 2 3 →