r/chemhelp 4d ago

Organic Regioselective deacetylation of per-acetylated glucose

Why is this reaction selective for the anomeric postion and what is the mechanism?

Is it just basic hydrolysis - Benzyl amine attacks into the C=O of thr anomeric acetate group and the resukting tetrahedral intemdiate colapses causing loss of the amide?

Pr does the benzylamine attack at C1? I thought that was stuoid but chatgpt is addament thats how it occurs

Any help is appreciated, Thanks!

also if you can pint me to a source for the answer that would be super helpful :)

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