Regioselective polycondensation of benzyl 2-amino-2-deoxy-α-D-glucopyranoside hydrochloride with carbon dioxide

This paper reports the polycondensation of benzyl 2-amino-2-deoxy-α-D-glucopyranoside hydrochloride (1) with carbon dioxide using the triphenylphosphine/carbon tetrachloride/DBU system as a condensing agent to give poly(urethane) (2). The polycondensation of 1 with CO₂ was carried out in DMF solvent in the presence of the condensing agent under CO₂ atmosphere. From the NMR and IR analyses of the product, the polymerization proceeded regioselectively to form 2. The molecular weight was estimated as 2000–3000 by GPC measurement after acetylation of 2, corresponding to DP = 5–8.