Abstract
In order to clarify whether or not direct O-1β→ -6 acyl migration in O-acyl-D-glucose derivatives really occurs, 3-O-methyl-1-O-myristoyl-β-D-glucopyranose and 3-deoxy-1-O-myristoyl-β-D-glucopyranose were synthesized and their acyl migration was examined under thermal, solvolytic, and base- and acid-catalyzed conditions. Neither compound showed any tendency for acyl migration under these conditions (only partial solvolysis was observed under solvolytic conditions). Consequently, it was concluded that O-1β→ -6 acyl migration does not occur directly, but proceeds through the path O-1β→ -3→ -6.
