title: Total synthesis of Lewis(X) using a late-stage crystalline intermediate.
abstract: Herein, we report on a highly efficient synthesis of a crystalline protected Lewis(X) trisaccharide that was converted to Lewis(X) following global deprotection. The trisaccharide was prepared in a highly convergent synthesis (seven steps, longest linear sequence) and in a 38% overall yield using a strategy that involved the regioselective glycosylation of a GlcNAc acceptor with a galactose thioglycoside donor, followed by fucosylation of the remaining free GlcNAc hydroxyl as key steps. The core trisaccharide also has the potential to be converted to other members of the Type-2 Lewis family of antigens due to the orthogonal nature of the protecting groups employed.
authors.affiliation: School of Chemical and Physical Sciences, Victoria University of Wellington, PO Box 600, Wellington, New Zealand.
authors.forename: Stefan
authors.initials: S
authors.lastname: Munneke
authors.affiliation: Ferrier Institute, Victoria University of Wellington, PO Box 600, Wellington, New Zealand.
authors.forename: Gavin F
authors.initials: GF
authors.lastname: Painter
authors.affiliation: Callaghan Innovation, PO Box 31310, Lower Hutt, New Zealand.
authors.forename: Graeme J
authors.initials: GJ
authors.lastname: Gainsford
authors.affiliation: School of Chemical and Physical Sciences, Victoria University of Wellington, PO Box 600, Wellington, New Zealand.
authors.forename: Bridget L
authors.initials: BL
authors.lastname: Stocker
authors.affiliation: School of Chemical and Physical Sciences, Victoria University of Wellington, PO Box 600, Wellington, New Zealand. Electronic address: mattie.timmer@vuw.ac.nz.
authors.forename: Mattie S M
authors.initials: MS
authors.lastname: Timmer
mesh_terms: D006031:Glycosylation; D016256:Lewis X Antigen / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D016256:Lewis X Antigen; D014312:Trisaccharides
keywords: Carbohydrate; Glycosylation; Lewis(X); Synthesis