Abstract
The trisaccharide 2,3,4-O-tribenzyl-a-L-rhamnosyl- (1→3)-4-O-acetyl-2-O-benzoyl-(1→2)-4-O-acetyl-3-O-benzoyl- a-L-rhamnosyl-1-(4-tolyl)thio-a-L-rhamnopyranoside was pre- pared from the thio-sugar 1-(4-tolyl)thio-a,b-L-rhamnopyranoside from the nonreducing end to the reducing end. The two acceptors possessing 2- and 3-OH groups for the construction of the trisaccha- ride were obtained from a 2,3-benzylidine-protected thio-sugar in a one-pot deprotection manner in a respective ratio of 1:2.5. As do- nors for glycosylation, the thio-sugars of both mono- and disaccha- rides were converted to trichloroacetimido rhamnosides. Through this chemoselective strategy, a trisaccharide was obtained that re- tained an anomeric thio group for coupling with ceramide moieties. Bioassays are in progress.
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