An Operationally Simple and Efficient Synthesis of Orthogonally Protected L-threo-beta-Hydroxyasparagine.
A synthesis of orthogonally protected L-threo-beta-hydroxyasparagine from L-aspartic acid is reported. Iodocyclization of 3-benzoylaminoaspartic acid provided an intermediate oxazoline dicarboxylate that was efficiently hydrolyzed to L-threo-beta-hydroxyaspartic acid. The synthetic route for conversion of the free beta-hydroxy-alpha-amino acid into the target compound is highly efficient and amenable to preparation various orthogonally protected asparagine derivatives, on a multiple gram scale.
Guzmán-Martinez
Aikomari
A
Department of Chemistry and Biochemistry, University of California at San Diego, 9500 Gilman Drive, La Jolla, CA 92093.
Vannieuwenhze
Michael S
MS