Organic synthesis in pursuit of immunology: large-scale synthesis of peracetylated GM2 glycosylamino acid for preparation of a multiantigenic prostate cancer vaccine.

We describe herein the stereo-controlled, large-scale synthesis of peracetylated GM2 glycosylamino acid. Key features of the synthesis include a newly modified [1+3] coupling reaction and an olefin cross-metathesis-hydrogenation sequence. The GM2 glycosylamino acid is now ready for incorporation into a hexavalent prostate cancer vaccine construct.