Synthesis and characterization of polyester dendrimers from acetoacetate and acrylate

被引:17
作者
Hirayama, Y
Nakamura, T
Uehara, S
Sakamoto, Y
Yamaguchi, K
Sei, Y
Iwamura, M
机构
[1] Toho Univ, Dept Biomol Sci, Funabashi, Chiba 2748510, Japan
[2] Toho Univ, Sch Pharmaceut Sci, Funabashi, Chiba 2748510, Japan
[3] Chiba Univ, Ctr Chem Anal, Inage Ku, Chiba 2638522, Japan
关键词
D O I
10.1021/ol0482184
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New aliphatic polyester-type dendrimers were synthesized using a new AB(2)-type building block 3, prepared from benzyl acetoacetate and 2 equiv of tert-butyl acrylate by acelloacetic acid ester synthesis. The reiterative [deprotection by HCO2H, then EDCI/DMAP coupling] sequence using divergent growth method gave [G1]-4tBu-[G5]-64tBu dendrimers. C-13 NMR relaxation time (T-1) measurements on the carboxy carbons show that the extended chain conformations are predominant in CDCl3.
引用
收藏
页码:525 / 528
页数:4
相关论文
共 19 条
[1]   Hybrid dendritic-linear polyester-ethers for in situ photopolymerization [J].
Carnahan, MA ;
Middleton, C ;
Kim, J ;
Kim, T ;
Grinstaff, MW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (19) :5291-5293
[2]   Synthesis and characterization of polyether-ester dendrimers from glycerol and lactic acid [J].
Carnahan, MA ;
Grinstaff, MW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (12) :2905-2906
[3]   Structure and conformation of DAB dendrimers in solution via multidimensional NMR techniques [J].
Chai, MH ;
Niu, YH ;
Youngs, WJ ;
Rinaldi, PL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (20) :4670-4678
[4]   Polyester dendritic systems for drug delivery applications:: In vitro and in vivo evaluation [J].
De Jesús, OLP ;
Ihre, HR ;
Gagne, L ;
Fréchet, JMJ ;
Szoka, FC .
BIOCONJUGATE CHEMISTRY, 2002, 13 (03) :453-461
[5]  
Frechet J. M. J., 2002, DENDRIMERS OTHER DEN
[6]   Dendrimers and other dendritic macromolecules:: From building blocks to functional assemblies in nanoscience and nanotechnology [J].
Fréchet, JMJ .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2003, 41 (23) :3713-3725
[7]   FUNCTIONAL POLYMERS AND DENDRIMERS - REACTIVITY, MOLECULAR ARCHITECTURE, AND INTERFACIAL ENERGY [J].
FRECHET, JMJ .
SCIENCE, 1994, 263 (5154) :1710-1715
[8]   An alternative synthetic approach toward dendritic macromolecules:: Novel benzene-core dendrimers via alkyne cyclotrimerization [J].
Hecht, S ;
Fréchet, JMJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (16) :4084-4085
[9]   Fast and convenient divergent synthesis of aliphatic ester dendrimers by anhydride coupling [J].
Ihre, H ;
De Jesús, OLP ;
Fréchet, JMJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (25) :5908-5917
[10]   Morphology-dependent photochemical events in aryl ether dendrimer porphyrins: Cooperation of dendron subunits for singlet energy transduction [J].
Jiang, DL ;
Aida, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (42) :10895-10901