116233-68-2Relevant articles and documents
Synthesis of 1-O-Methyl-β,D-ezoaminouoic Acid
Knapp, Spencer,Levorse, Anthony T.,Potenza, Joseph A.
, p. 4773 - 4779 (2007/10/02)
The synthesis of the title compound from the Diels-Alder adduct of diethyl ketomalonate and 1,3-butadiene (nine steps, 13percent overall yield) is described.The key step is a transannular "bromolactamization" reaction, which sets up the stereocontrolled functionalization of the pyran ring.The use of resolved p-methoxyenethylamine as the source of the amino group allows the synthesis of both the D (natural) and L (unnatural) series amino sugars.