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Peer Reviewed Journal
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Gemma, Emiliano,Lahmann, Martina,Oscarson, Stefan;
2006
Synthesis of monodeoxy analogs of the trisaccharide a-D-Glcp-(1->3)-a-D-Manp-(1->2)-a-D-ManpOMe recognized by Calreticulin/Calnexin
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Six (3,4,4',6',3'' or 6'')-monodeoxy analogs of the title trisaccharide have been prepd. utilizing monodeoxy monosaccharide precursors. The reducing end deoxy derivs. were synthesized by N-iodosuccinimide/silver trifluoromethanesulfonate (NIS/AgOTf)-promoted couplings of a common disaccharide thioglycoside donor to suitably protected monodeoxy acceptors affording two of the trisaccharides. The non-reducing end deoxy derivs. could similarly be produced by halide-assisted glycosylations of a common disaccharide acceptor with monodeoxy glycosyl bromide donors to yield, after removal of protecting groups, another two of the target trisaccharides. The analogs with the deoxy function in the middle mannose residue, were obtained through orthogonal halide-assisted coupling of tetrabenzyl-glucopyranosyl bromide to monodeoxy thioglycoside acceptors to give thioglycoside disaccharides, which subsequently were used as donors in NIS/AgOTf-promoted couplings to a common 2-hydroxy-mannose acceptor to afford trisaccharides; deprotection yielded the final target trisaccharides. [on SciFinder (R)]
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