Synthesis and characterization of polyester dendrimers from acetoacetate and acrylate

Yuuki Hirayama; Taisuke Nakamura; Satoshi Uehara; Yohko Sakamoto; Kentaro Yamaguchi; Yoshihisa Sei; Michiko Iwamura

doi:10.1021/ol0482184

Synthesis and characterization of polyester dendrimers from acetoacetate and acrylate

Org Lett. 2005 Feb 17;7(4):525-8. doi: 10.1021/ol0482184.

Authors

Yuuki Hirayama¹, Taisuke Nakamura, Satoshi Uehara, Yohko Sakamoto, Kentaro Yamaguchi, Yoshihisa Sei, Michiko Iwamura

Affiliation

¹ Department of Biomolecular Science and School of Pharmaceutical Sciences, Toho University, Miyama 2-2-1, Funabashi, Chiba 274-8510, Japan.

PMID: 15704885
DOI: 10.1021/ol0482184

Abstract

New aliphatic polyester-type dendrimers were synthesized using a new AB2-type building block 3, prepared from benzyl acetoacetate and 2 equiv of tert-butyl acrylate by acetoacetic acid ester synthesis. The reiterative [deprotection by HCO2H, then EDCI/DMAP coupling] sequence using divergent growth method gave [G1]-4tBu-[G5]-64tBu dendrimers. 13C NMR relaxation time (T1) measurements on the carboxy carbons show that the extended chain conformations are predominant in CDCl3. [structure: see text]

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetoacetates*
Acrylates*
Dendrimers / chemical synthesis*
Dendrimers / chemistry
Magnetic Resonance Spectroscopy
Models, Molecular
Polyesters / chemical synthesis*
Polyesters / chemistry
Spectrometry, Mass, Electrospray Ionization

Substances

Acetoacetates
Acrylates
Dendrimers
Polyesters
acetoacetic acid