Abstract
Glycosylation of 4-nitrophenyl 2-acetamido-6- O-tert-butyldiphenylsilyl-2-deoxy-1-thio-β- d-glucopyranoside with phenyl 2,3,4,6-tetra- O-benzoyl-1-thio-β- d-galactopyranoside in the presence of NIS and TfOH as catalyst gave the lactosamine derivative regiospecifically in high yield. Further 3- O-fucosylation with phenyl 2,3,4-tri- O-benzyl-1-thio-β- l-fucopyranoside using DMTST as promoter afforded the Le x trisaccharide intermediate. The latent glycosyl donor was transformed into its active form ( p-acetamidothiophenyl) by reduction with zinc in acetic acid and N-acetylation. Glycosidation with p-nitrothiophenyl lactoside acceptor in the presence of NIS/TfOH as catalyst gave the Le x pentasaccharide in 71% yield.
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