Hydroxyl group orientation affects hydrolysis rates of methyl α-septanosides

Hydrolysis rates for three related methyl α-septanosides were obtained. The septanosides were synthesized via mCPBA epoxidation and methanolysis of d-mannose, d-galactose, and d-glucose-based oxepines. The rate of hydrolysis correlates with the orientation of hydroxyl groups on the septanose ring in a manner analogous to pyranosides.