M. Okada, H. Sumitomo, Yasuhito Hishida
Sep 1, 1983
Citations
0
Influential Citations
13
Citations
Journal
Macromolecular Chemistry and Physics
Abstract
A new D,L-polysaccharide, 4-deoxy-(16)-α-D,L-xylo-hexopyranan (3), containing two hydroxyl groups in its repeating unit was synthesized, starting from 3,4-dihydro-2 H-pyran-2-carbaldehyde (4) (Acrolein dimer). The monomer, a bicyclic acetal, 3(a),4(a)-bis(benzyloxy)-6,8-dioxabicyclo[3.2.1]octane (1) was prepared from the starting material via six step reactions. The cationic ring-opening polymerization of 1 was effectively achieved by using antimony pentachloride or trifluoromethanesulfonic acid as initiators to afford the polyacetal 2 with number average molecular weights of up to 1,2 · 105. Debenzylation of 2 with sodium metal in liquid ammonia gave rise to a white powdery polymer identified as 3 by 13C-NMR spectroscopy. The synthetic polysaccharide 3 melting in the range of 90 to 103°C was found to be soluble in dimethyl sulfoxide and water, and insoluble in other common organic solvents. Water sorption of 3 was measured at different relative humidities between 32 and 97% and compared with those of natural dextran and a synthetic polysaccharide having an analogous structure.