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Solid Phase Stepwise Synthesis of Polyethylene Glycols
Author(s) -
Khanal Ashok,
Fang Shiyue
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201703004
Subject(s) - polyethylene glycol , monomer , solid phase synthesis , trifluoroacetic acid , peg ratio , ethylene glycol , polymer chemistry , chemistry , polystyrene , ether , organic chemistry , polymer , peptide , biochemistry , finance , economics
Abstract Polyethylene glycol (PEG) and derivatives with eight and twelve ethylene glycol units were synthesized by stepwise addition of tetraethylene glycol monomers on a polystyrene solid support. The monomer contains a tosyl group at one end and a dimethoxytrityl group at the other. The Wang resin, which contains the 4‐benzyloxy benzyl alcohol function, was used as the support. The synthetic cycle consists of deprotonation, Williamson ether formation (coupling), and detritylation. Cleavage of PEGs from solid support was achieved with trifluoroacetic acid. The synthesis including monomer synthesis was entirely chromatography‐free. PEG products including those with different functionalities at the two termini were obtained in high yields. The products were analyzed with ESI and MALDI‐TOF MS and were found close to monodispersity.