Free radical polymerization of a sugar residue-carrying styryl monomer with a lipophilic alkoxyamine initiator: synthesis of a well-defined novel glycolipid

Controlled free radical polymerization of N-p-vinylbenzyl-2,3,5,6-tetra-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-D-gluconamide (Ac-VLA) was achieved by the nitroxide-mediated free radical polymerization with a lipophilic alkoxyamine “initiator” with a dioctadecyl group in 1,2-dichloroethane at 90°C. The polymerization proceeds in a “living” fashion, providing Ac-VLA polymers with low polydispersity. The hydrolysis of the polymers results in well-defined glycopolymer-carrying amphiphiles, viz., artificial “glycolipids”.