Synthesis of upper rim calix[4]arene divalent glycoclusters via amide bond conjugation

被引:26
作者
Schädel, U [1 ]
Sansone, F [1 ]
Casnati, A [1 ]
Ungaro, R [1 ]
机构
[1] Univ Parma, Dipartimento Chim Organ & Ind, I-43100 Parma, Italy
关键词
calix[4]arene; neoglycoconjugates; glycoside; amide bond;
D O I
10.1016/j.tet.2004.11.048
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthetic routes for linking two sugar units at the upper rim of cone calix[4]arenes, through the formation of amide bonds, have been explored. Steric effects prevent the coupling of calix[4]arene dicarboxylic acid with simple aminoglycosides, whereas the corresponding reaction with carbohydrates bearing a two or three carbon atoms spacer, terminating with a primary amino group, allows the synthesis of several difunctionalized calix[4]arene neoglycoconjugates, attractive in chemical glycobiology and supramolecular chemistry. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1149 / 1154
页数:6
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