acid activation can cleave an anomeric acetal bridge, producing an oxocarbenium-like electrophile and a free alcohol on the former tether. methanol capture produces a methyl acetal; anomeric stereochemistry and chair preference must be distinguished.
Acetal cleavage can depend on alignment of an endocyclic oxygen lone pair with the exocyclic C–O leaving bond. Conformational restriction can therefore give different hydrolysis rates for anomers without changing the leaving group.
Protonation enables alcohol departure, water capture and carbonyl regeneration, often through oxocarbenium and hemiacetal intermediates.
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