Ring-Opening Polymerization of a 1, 6-Anhydro Sugar Having a Long Alkyl Chain

Abstract

A new monomer, 1, 6-anhydro-2, 4-di-O-benzy1-3-O-dodecyl-β-D-glucopyranose (2), was prepared from 1, 6-anhydro-2, 4-di-O-benzyl-β-D-glucopyranose (1) and 1-bromododecane, and was polymerized in the presence of a PF⁵ initiator at 60°C. The polymerization reactivity of (2 ) was high and a high molecular weight polymer with intrinsic viscosity (η) of 1.29was obtained in a quantitative yield in a short time. The 1H- and ¹³C-NMR spectra indicated that the polymer was stereoregular 2, 4-di-O-benzy1-3-O-dodecyl-(1→6)-α-D-glucopyrana (3), which would serve as a precursor for synthesizing a polymer model of glycolipids. Regioselectively Modified Stereoregular Polysaccharides. V.