Direct glycosylation of protected O-tritylserine esters and oligopeptides

Article abstract of DOI:10.1016/0008-6215(95)00097-D

N-Fmoc-3-O-Tr-L-serine methyl and benzyl esters, as well as a tripeptide FmocAlaSer(Tr)GlyOBn were directly glycosylated by 3,4,6-tri-O-acetyl-1,2-O-(1-cyanoethylidene)-α-D-galactopyranose in the presence of TrClO4 in dichloromethane, yielding 32-57percent of N-Fmoc-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-L-serine esters and the corresponding tripeptide.Keywords: Glycosylation; N-9-Fluorenylmethoxycarbonyl-O-tritylserine esters; Serine glycosides; Serine glycopeptides; Cyanoethylidene condensation