title: Synthesis of Human Cancer Associated Globo-H (MBr1) Glycosylamino Acid: Some Mechanistic and Conformational Reinvestigations.
abstract: The synthesis of an extended globo-H (MBr1 antigen) in the form of a glycosylamino acid is reported. By careful NMR analysis, we found an interesting conformational "flip" on the E ring of some synthetic intermediates. An explanation offered for the successful [3+3] coupling of ABC acceptor 11 and DEF donor 10 possessing a C4 free hydroxyl to produce β-galactoside in azaglycosidations is reinforced.
authors.affiliation: Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Ave., New York, NY 10065.
authors.forename: Jianglong
authors.initials: J
authors.lastname: Zhu
authors.forename: Qian
authors.initials: Q
authors.lastname: Wan
authors.forename: Guangbin
authors.initials: G
authors.lastname: Yang
authors.forename: Ouathek
authors.initials: O
authors.lastname: Ouerfelli
authors.forename: Samuel J
authors.initials: SJ
authors.lastname: Danishefsky