Total synthesis and proof of structure of a human breast tumor (globo-H) antigen

A total synthesis of the Hakomori MBr1 antigen, heavily expressed on human breast tumors, was performed. The construction required the assembly of four glycals and an L-fucose derivative. The sensitivity of the stereochemistry of sulfonamido galactosylation by a terminal galactose ring as a function of the state of protection status of its C4 alcohol was exploited in a crucial step. A linker domain was established for the purpose of developing a functional vaccine.