A concise synthesis of the O-glycosylated amino acid building block;: using phenyl selenoglycoside as a glycosyl donor

A new glycosylation methodology for synthesizing a protected TF antigen is described. The key step is to use phenyl selenoglycoside as a glycosyl donor, thereby successfully establishing O-linked Fmoc-protected threoninyl monosaccharide in an excellent yield with high alpha selectivity. From protected D-galactal, a protected TF antigen building block is obtained in 40% total yield. (C) 2000 Elsevier Science Ltd. All rights reserved.