Synthesis of optically inactive cellulose via cationic ring-opening polymerization

Cellulose, which comprises D-glucose and L-glucose (D,L-cellulose), was synthesized from (1D) (1L) via cationic ring-opening polymerization. Specifically, the copolymerization of 3-O-benzyl-2,6-di-O-pivaloyl-β-D-glucopyranoside (2D) (2L), compounds 1D 1L, respectively, in a 1:1 ratio, afforded 3-O-benzyl-2,6-di-O-β-D,L-glucopyranan (3DL) with degree polymerization (DPn) 28.5 (Mw/Mn = 1.90) quantitative yield. The deprotection compound 3DL subsequent acetylation proceeded smoothly to afford acetylated 4DL DPn 18.6 2.08). specific rotation + 0.01°, suggesting that optically inactive cellulose triacetate. Furthermore, before acetylation, an comprising almost racemic mixture L-glucose. Compound amorphous polymer. This is first reported synthesis D,L-cellulose.