Abstract
Synthesis of three kinds of 6-O-sulfated sLe x glyco probes with their relevance to ligand processing pathway of L-selectin has been described. The glycosylation of the suitably protected hexasaccharide acceptor 6 with the sialyl-a-(2→3)-D-galactopyranosyl SMe donors (3 and 4) using dimethyl(methylthio)sulfonium triflate (DMTST), afforded the protected tetrasaccharides 7 and 8, respectively. Removal of all the benzyl protecting groups and the subsequent acetylation afforded the sLe x derivatives (9 and 10), which were converted to the target compounds (15 and 16) by the selective removal of 4-methoxyphenyl group, followed by 6-O-sulfation of the GlcNAc residue, and removal of all the protective groups under basic conditions. Finally 16 was lactamized with HBTU and HOBT, to give the desired target compound 17.
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