Transition metal catalyzed neoglycoconjugate syntheses

被引:56
作者
Roy, R [1 ]
Das, SK [1 ]
Dominique, R [1 ]
Trono, MC [1 ]
Hernández-Mateo, F [1 ]
Santoyo-González, F [1 ]
机构
[1] Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
D O I
10.1351/pac199971040565
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Carbohydrate-containing clusters of various valency were synthesized using transition metal-catalyzed reactions. Thus, Grubbs' ruthenium benzylidene catalyst was used successfully in olefin self-and cross-metathesis reactions from both O-and C-alkenyl glycopyranosides. The reaction was also used to generate C-linked pseudodisaccharides. Oxidative dimerization of terminal alkynes such as 2-propynyl glycopyranosides was accomplished with coupling between 2-propynyl and 4-iodophenyl mannopyranosides afforded novel sugar-rods useful in studying carbohydrate-protein interactions. Cyclotrimerization of terminal as well as symmetrical alkyne derivatives with dicobalt octacarbonyl allowed access to trimers and hexamers, respectively.
引用
收藏
页码:565 / 571
页数:7
相关论文
共 47 条
[41]   Catalytic applications of transition metals in organic synthesis [J].
Tonks, L ;
Williams, JMJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (21) :3637-3652
[42]   BIOLOGICAL ROLES OF OLIGOSACCHARIDES - ALL OF THE THEORIES ARE CORRECT [J].
VARKI, A .
GLYCOBIOLOGY, 1993, 3 (02) :97-130
[43]   COBALT-MEDIATED [2+2+2]-CYCLOADDITIONS - A MATURING SYNTHETIC STRATEGY [J].
VOLLHARDT, KPC .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (08) :539-556
[44]   INTERACTION OF GLYCOSIDES AND SACCHARIDES WITH ANTIBODY TO CORRESPONDING PHENYLAZO GLYCOSIDES [J].
YARIV, J ;
GRAF, L ;
RAPPORT, MM .
BIOCHEMICAL JOURNAL, 1962, 85 (02) :383-&
[45]  
Zanini D, 1998, CARBOHYDRATE MIMICS, P385
[46]   Synthesis of new alpha-thiosialodendrimers and their binding properties to the sialic acid specific lectin from Limax flavus [J].
Zanini, D ;
Roy, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (09) :2088-2095
[47]   Practical synthesis of starburst PAMAM α-thiosialodendrimers for probing multivalent carbohydrate-lectin binding properties [J].
Zanini, D ;
Roy, R .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10) :3486-3491