Synthesis of Human Cancer Associated Globo-H (MBr1) Glycosylamino Acid: Some Mechanistic and Conformational Reinvestigations

Heterocycles. 2009 Apr 1;79(1):441-449. doi: 10.3987/COM-08-S(D)82.

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.