Novel dendritic cores based on thiacalix[4]arene derivatives

被引:25
作者
Appelhans, D
Stastny, V
Komber, H
Voigt, D
Voit, B
Lhoták, P
Stibor, I
机构
[1] Inst Polymer Res Dresden, Dresden, Germany
[2] Inst Chem Technol, Dept Organ Chem, Prague 16628 6, Czech Republic
关键词
thiacalixarenes; benzylic spacer; dendritic core; amino surface group;
D O I
10.1016/j.tetlet.2004.07.085
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Thiacalix[4]arenes possessing carboxylic groups were used for the design of potential dendritic cores with amino surface groups. The known tetraacetic acid in the 1,3-alternate conformation gave the desired product in very low yield because of steric hindrance on thiacalix[4]arene moiety. Therefore, synthetic strategy based on withdrawing of the carboxyl groups via benzylic spacer from the thiacalix[4]arene moiety was successfully applied for the realization of novel thiacalix[4]arenes bearing two or four protected lysine units. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7145 / 7149
页数:5
相关论文
共 25 条
[11]   SYNTHESIS AND METAL-BINDING PROPERTIES OF OLIGO-CALIXARENES - AN APPROACH TOWARDS THE CALIX[4]ARENE-BASED DENDRIMERS [J].
LHOTAK, P ;
SHINKAI, S .
TETRAHEDRON, 1995, 51 (28) :7681-7696
[12]   Chemistry of thiacalixarenes [J].
Lhoták, P .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (08) :1675-1692
[13]   Synthesis and 1H NMR complexation study of thiacalix[4]arene tetraacetates [J].
Lhoták, P ;
Stastny, V ;
Zlatusková, P ;
Stibor, I ;
Michlová, V ;
Tkadlecová, M ;
Havlícek, J ;
Sykora, J .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2000, 65 (05) :757-771
[14]   Unprecedented formation of lactone derivatives in thiacalix[4]arene series [J].
Lhoták, P ;
Dudic, M ;
Stibor, I ;
Petrícková, H ;
Sykora, J ;
Hodacová, J .
CHEMICAL COMMUNICATIONS, 2001, (08) :731-732
[15]  
Mandolini L., 2000, Calixarenes in Action
[16]   Covalently linked multi-calixarenes [J].
Mogck, O ;
Parzuchowski, P ;
Nissinen, M ;
Böhmer, V ;
Rokicki, G ;
Rissanen, K .
TETRAHEDRON, 1998, 54 (34) :10053-10068
[17]   Thiacalixarene. A new molecular scaffold for host molecules [J].
Morohashi, N ;
Iki, N ;
Miyano, S .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2002, 60 (06) :550-562
[18]  
Narumi F, 2000, ENANTIOMER, V5, P83
[19]   Thiacalixarenes - A new class of synthetic receptors [J].
Shokova, EA ;
Kovalev, VV .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 39 (01) :1-28
[20]   Synthesis of (thia)calix[4]arene oligomers:: towards calixarene-based dendrimers [J].
Stastny, V ;
Stibor, I ;
Dvoráková, H ;
Lhoták, P .
TETRAHEDRON, 2004, 60 (15) :3383-3391