Use of a phenyl 1-selenogalactofuranoside as glycosyl donor for the synthesis of galactofuranosyl-containing disaccharides

Article abstract of DOI:10.1016/S0008-6215(97)10016-7

The use of acetylated phenyl 1-seleno-β-D-galactofuranoside as a glycosyl donor for the synthesis of protected D-Galf-β-(1 → 3)-α-D-Manp as its methyl or ethylthio glycoside has been demonstrated. Activation of the selenoglycoside over a thioglycoside acceptor by NIS/TfOH is extremely selective and gives the ethylthio disaccharide in 91% yield. The parent disaccharide is found as a terminal and branched unit in the lipopeptidophosphoglycan oligosaccharides of the protozoan Trypanosoma cruzi, the causative agent of Chagas' disease.