title: Carbasugar analogues of galactofuranosides: β-O-linked derivatives and towards β-S-linked derivatives.
abstract: A selectively protected carbasugar analogue of β-galactofuranose was synthesised from glucose using ring-closing metathesis as the key step. The carbasugar was converted into an α-galacto configured 1,2-epoxide, which was an effective electrophile in Lewis acid catalysed coupling reactions with alcohols. The epoxide was opened with regioselective attack at C-1 to give β-galacto configured C-1 ethers. Using carbohydrates as nucleophiles, we synthesised a number of pseudodisaccharides. The epoxide was also regioselectively opened at C-1 with a sulfur nucleophile under basic conditions to give a β-galacto configured C-1 thioether.
authors.affiliation: Department of Organic Chemistry, The Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden.
authors.forename: Jens
authors.initials: J
authors.lastname: Frigell
authors.forename: Lars
authors.initials: L
authors.lastname: Eriksson
authors.forename: Ian
authors.initials: I
authors.lastname: Cumpstey
mesh_terms: D002241:Carbohydrates / Q000737:chemistry*; D004187:Disaccharides / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry; D005697:Galactosides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
chemical_list: D002241:Carbohydrates; D004187:Disaccharides; D004852:Epoxy Compounds; D005697:Galactosides