Nachbargruppenbeteiligungen bei der substitution von 2-amino-2-desoxy-α-d-glucopyranosiden in der 3-stellung

Neighboring group participation severely restricted nucleophilic substitution of N-protected 2-amino-2-deoxy-3-O-mesyl-α-D-glucopyranosides with azide ion. N-acetyl as blocking group led to the formation of the oxazoline $\text{3}$ while from N-dinitrophenylderivatives epimers were formed via the aziridine $\text{11}$.