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Communication | Special issue | Vol 79, No. 1, 2009, pp.441-449
Published online, 9th January, 2009
DOI: 10.3987/COM-08-S(D)82
Synthesis of Human Cancer Associated Globo-H (MBr1) Glycosylamino Acid: Some Mechanistic and Conformational Reinvestigations

Jianglong Zhu, Qian Wan, Guangbin Yang, Ouathek Ouerfelli, and Samuel J. Danishefsky*

*Department of Chemistry, Columbia University, 3000 Broadway, New York, NY 10027, U.S.A.


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.