High-yielding microwave-assisted synthesis of triazole-linked glycodendrimers by copper-catalyzed [3+2] cycloaddition

被引：114

作者：

Joosten, JAF ^{[1
]}

Tholen, NTH ^{[1
]}

El Maate, FA ^{[1
]}

Brouwer, AJ ^{[1
]}

van Esse, GW ^{[1
]}

Rijkers, DTS ^{[1
]}

Liskamp, RMJ ^{[1
]}

Pieters, RJ ^{[1
]}

机构：

[1] Utrecht Inst Pharmaceut Sci, Dept Med Chem, NL-3508 TB Utrecht, Netherlands

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 15期

关键词：

carbohydrates; glycosides; dendrimers; cycloaddition; microwave activation;

D O I：

10.1002/ejoc.200500216

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile and high-yielding synthesis of multivalent 1,4-disubstituted 1,2,3-triazole-linked glycodendrimers is described. Azido carbohydrates are linked by a Cu-I-catalyzed [3+2] cycloaddition reaction to dendritic acetylenes using microwave irradiation. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).

引用

页码：3182 / 3185

页数：4

共 51 条

[1] André S, 2001, CHEMBIOCHEM, V2, P822, DOI 10.1002/1439-7633(20011105)2:11<822::AID-CBIC822>3.0.CO
[2] 2-W
[3] Synthesis and cholera toxin binding properties of multivalent GM1 mimics
Arosio, D
Vrasidas, I
Valentini, P
Liskamp, RMJ
Pieters, RJ
Bernardi, A
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (14) : 2113 - 2124
[4] High-avidity, low-affinity multivalent interactions and the block to polyspermy in Xenopus laevis
Arranz-Plaza, E
Tracy, AS
Siriwardena, A
Pierce, JM
Boons, GJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (44) : 13035 - 13046
[5] A convergent synthesis of a carbohydrate-containing dendrimer
Ashton, PR
Boyd, SE
Brown, CL
Jayaraman, N
Stoddart, JF
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (07): : 732 - 735
[6] Adhesion inhibition of F1C-fimbriated Escherichia coli and Pseudomonas aeruginosa PAK and PAO by multivalent carbohydrate ligands
Autar, R
Khan, AS
Schad, M
Hacker, J
Liskamp, RMJ
Pieters, RJ
[J]. CHEMBIOCHEM, 2003, 4 (12) : 1317 - 1325
[7] A new chemical probe for proteomics of carbohydrate-binding proteins
Ballell, L
Alink, KJ
Slijper, M
Versluis, C
Liskamp, RMJ
Pieters, RJ
[J]. CHEMBIOCHEM, 2005, 6 (02) : 291 - 295
[8] Synthesis of readily modifiable cyclodextrin analogues via cyclodimerization of an alkynyl-azido trisaccharide
Bodine, KD
Gin, DY
Gin, MS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (06) : 1638 - 1639
[9] Synthesis of novel dendrimeric systems containing NLO ligands
Brouwer, AJ
Liskamp, RMJ
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (03) : 487 - 495
[10] Brouwer AJ, 2001, EUR J ORG CHEM, V2001, P1903

← 1 2 3 4 5 6 →