title: Study of the endocyclic versus exocyclic C-O bond cleavage pathways of α- and β-methyl furanosides.
abstract: The activation and ring-opening of methyl furanosides in the four natural sugar scaffolds (ribo, lyxo, arabino, and xylo) efficiently afforded acyclic thioacetals with high S(N)2-like selectivity at the acetal center in the presence of Me2BBr and thiophenol. The stereochemical outcome of these reactions provides important mechanistic insights into the activation pathway of five-membered semicyclic acetals. The thioacetal products should find applications in oligosaccharides synthesis and allow further development of acyclic strategies for the synthesis of novel nucleoside analogues.
authors.affiliation: Bio-organic Chemistry, Institut de recherches cliniques de Montréal, Montréal, Québec, Canada H2W 1R7.
authors.forename: Olivier
authors.initials: O
authors.lastname: St-Jean
authors.forename: Michel
authors.initials: M
authors.lastname: Prévost
authors.forename: Yvan
authors.initials: Y
authors.lastname: Guindon
mesh_terms: D000080:Acetals / Q000138:chemical synthesis* / Q000737:chemistry; D005632:Fructose / Q000031:analogs & derivatives / Q000737:chemistry*; D015394:Molecular Structure; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000080:Acetals; D013438:Sulfhydryl Compounds; D005632:Fructose