Galabiosyl donors; efficient synthesis from 1,2,3,4,6-penta-O-acetyl-β-d-galactopyranose Original Research Article

1,2,3,4,6-Penta-O-acetyl-β-d-galactopyranose was transformed into phenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-d-galactopyranoside (5) and 4-methoxyphenyl 2,3,6-tri-O-benzoyl-β-d-galactopyranoside (8) in 73% (two steps) and 58% (three steps) yield, respectively. Glycosylation of the acceptor 8 with donor 5 using N-iodosuccinimide–trimethylsilyl trifluoromethanesulfonate as promoter furnished the galabioside 9 (8.8 g) in 95% yield. Further transformations provided in high yields anomerically-activated galabiosides (thioglycoside (1), trichloroacetimidate (2), and bromosugar (3)) suitable for use as glycosyl donors in syntheses of galabiose-containing oligosaccharides. Several of the compounds reported here are crystalline, which greatly simplified purifications.