Convenient polymer-supported synthetic route to heterobifunctional polyethylene glycols.
Conventional synthesis of heterobifunctional poly(ethylene glycol) derivatives, especially of medium size, is a rather tedious task. A straightforward solid-phase methodology has been developed that is illustrated here by the synthesis of alpha-pyridyldithio-omega-hydroxy-poly(ethylene glycol)600. This derivative was prepared from resin-bound PEG600 with a global yield of 65% for 6 individual steps, i.e., with an average yield of 93%/step. Intermediate purification steps simply consisted of resin washing. Progress of each reaction toward completion could conveniently be monitored by 13C NMR of the resin-bound PEG derivatives. This example highlights both the versatility and efficiency of combining polymer-supported synthesis with direct 13C-NMR characterization of the intermediate compounds.
Bettinger
T
T
Laboratoire de Chimie Génétique associé CNRS/Université Louis Pasteur de Strasbourg, UMR 7514, Faculté de Pharmacie, BP 24, 67401 Illkirch Cedex, France.
Remy
J S
JS
Erbacher
P
P
Behr
J P
JP
D009682:Magnetic Resonance Spectroscopy; D011092:Polyethylene Glycols / Q000138:chemical synthesis* / Q000737:chemistry*; D011108:Polymers; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D013055:Spectrophotometry, Infrared
D011108:Polymers; D011725:Pyridines; C116456:pyridyldithio-hydroxy-poly(ethylene glycol)600; D011092:Polyethylene Glycols