Phenols-useful templates for the synthesis of bi-functional orthogonally protected dendron building blocks via solid phase Mitsunobu reaction

作者: Gary Gellerman , Sagit Shitrit , Tzachi Shalit , Orit Ganot , Amnon Albeck

DOI: 10.1016/J.TET.2009.11.106

关键词:

摘要: Bi-functional dendritic building blocks for convergent dendrimer growth were successfully synthesized from phenolic templates in the solid phase via a Mitsunobu reaction. Each arm of dendron block carries an orthogonally protected secondary amine along arm, and peripheral primary or phenol group (building type 1) tertiary junction with carboxyl groups 2). The synthetic routes reported this work are general applicable preparation diverse blocks, controlling protection, length, moieties. These novel units can form unusual architectures by solid-phase chemistry, which may be incorporated into specific complex structures expanding scope science.

参考文章(34)
Takayoshi Arai, Tetuya Sekiguti, Yoshimasa Iizuka, Shinobu Takizawa, Shigeru Sakamoto, Kentaro Yamaguchi, Hiroaki Sasai, A dendrimer-supported heterobimetallic asymmetric catalyst Tetrahedron: Asymmetry. ,vol. 13, pp. 2083- 2087 ,(2002) , 10.1016/S0957-4166(02)00573-6
K. R. Gopidas, A. R. Leheny, G. Caminati, Nicholas J. Turro, Donald A. Tomalia, Photophysical investigation of similarities between starburst dendrimers and anionic micelles Journal of the American Chemical Society. ,vol. 113, pp. 7335- 7342 ,(1991) , 10.1021/JA00019A034
Johan F. G. A. Jansen, E. W. Meijer, Ellen M. M. de Brabander-van den Berg, The dendritic box, shape-selective liberation of encapsulated guests Journal of the American Chemical Society. ,vol. 117, pp. 4417- 4418 ,(1995) , 10.1021/JA00120A032
Louis A. Carpino, Grace Y. Han, 9-Fluorenylmethoxycarbonyl amino-protecting group Journal of Organic Chemistry. ,vol. 37, pp. 3404- 3409 ,(1972) , 10.1021/JO00795A005
Edis Kasëmi, Wei Zhuang, Jürgen P. Rabe, Karl Fischer, Manfred Schmidt, Martin Colussi, Helmut Keul, Ding Yi, Helmut Cölfen, A. Dieter Schlüter, Synthesis of an anionically chargeable, high-molar-mass, second-generation dendronized polymer and the observation of branching by scanning force microscopy. Journal of the American Chemical Society. ,vol. 128, pp. 5091- 5099 ,(2006) , 10.1021/JA057964G
Muthukaman Nagarajan, Xiangshu Xiao, Smitha Antony, Glenda Kohlhagen, Yves Pommier, Mark Cushman, Design, Synthesis, and Biological Evaluation of Indenoisoquinoline Topoisomerase I Inhibitors Featuring Polyamine Side Chains on the Lactam Nitrogen Journal of Medicinal Chemistry. ,vol. 46, pp. 5712- 5724 ,(2003) , 10.1021/JM030313F
D A Tomalia, H Baker, J Dewald, M Hall, G Kallos, S Martin, J Roeck, J Ryder, P Smith, A New Class of Polymers: Starburst-Dendritic Macromolecules Polymer Journal. ,vol. 17, pp. 117- 132 ,(1985) , 10.1295/POLYMJ.17.117
Craig J. Hawker, Jean M. J. Frechet, Preparation of polymers with controlled molecular architecture. A new convergent approach to dendritic macromolecules Journal of the American Chemical Society. ,vol. 112, pp. 7638- 7647 ,(1990) , 10.1021/JA00177A027
Ian R Hardcastle, Amelia Moreno Barber, Jonathan H Marriott, Michael Jarman, Polymer-assisted solution-phase library synthesis of 4-alkoxy-2-hydroxy-3,5,6-trifluorobenzoic acids Tetrahedron Letters. ,vol. 42, pp. 1363- 1365 ,(2001) , 10.1016/S0040-4039(00)02252-8