1051942-01-8Relevant articles and documents
New access to 1-deoxynojirimycin derivatives via azide-alkene cycloaddition
Zhou, Ying,Murphy, Paul V.
supporting information; experimental part, p. 3777 - 3780 (2009/07/09)
(Chemical Equation Presented) The synthesis of 1-deoxynojirimycin (DNJ) derivatives is described from D-glucono-δ-lactone. The DNJ derivatives were obtained via a sequence that included a stereoselective intramolecular Huisgen reaction, decomposition to an aziridine, and its subsequent reaction with a nucleophile. Minimization of allylic strain in the transition state accounts for the stereoselectivity of the cycloaddition reaction.