Abstract
6-O-Tosyl (1, d. s. 0.94, 80% yield), 6-deoxy-6-iodo (2, d. s. 0.49, 86% yield) and 6-deoxy (3, d. s. 0.49, 50% yield) derivatives of N-acetylchitosan were prepared, and a 13C CP/MAS NMR spectral analysis was performed because no suitable solvent for 3 was found. The 13C signal for CH3 at C-6 in 3 was detected at 18.9 ppm, and that for C-4 in 1-3 appeared at 72.2-72.7ppm, which is in a higher magnetic field than those (82.5-86.0ppm) in N-acetylchitosan, 6-O-(ethylthio), 6-O-(benzylthio)- and 6-O-(methylthio)-thiocarbonyl derivatives, chitosan, and chitin. This strongly suggests a different molecular conformation for 1-3.
