title: Multigram-scale synthesis of l,d-heptoside using a Fleming-Tamao oxidation promoted by mercuric trifluoroacetate.
abstract: An efficient multigram-scale synthesis of methyl 2,3,4,6-tetra-O-benzyl-l-glycero-α-d-manno-heptopyranoside from methyl 2,3,4-tri-O-benzyl-α-d-mannopyranoside is reported. It involves a sequence of Swern oxidation, Grignard addition and Fleming-Tamao reactions. The resulting scaffold was used as a precursor to design a small library of clickable l-heptosides. This study shows that the use of mercuric bistrifluoroacetate is required both to accelerate and to cleanly perform the Fleming-Tamao oxidation, without side-reactions.
authors.affiliation: Department of Chemistry, University of Namur, Rue de Bruxelles 61, 5000, Namur, Belgium.
authors.forename: Tianlei
authors.initials: T
authors.lastname: Li
authors.affiliation: Department of Chemistry, University of Namur, Rue de Bruxelles 61, 5000, Namur, Belgium.
authors.forename: Abdellatif
authors.initials: A
authors.lastname: Tikad
authors.affiliation: Department of Chemistry, University of Namur, Rue de Bruxelles 61, 5000, Namur, Belgium.
authors.forename: Maxime
authors.initials: M
authors.lastname: Durka
authors.affiliation: The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, 202, Sha-chong South Road, Guiyang, 550002, PR China.
authors.forename: Weidong
authors.initials: W
authors.lastname: Pan
authors.affiliation: Department of Chemistry, University of Namur, Rue de Bruxelles 61, 5000, Namur, Belgium. Electronic address: stephane.vincent@unamur.be.
authors.forename: Stéphane P
authors.initials: SP
authors.lastname: Vincent
mesh_terms: D057930:Click Chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006539:Heptoses / Q000138:chemical synthesis* / Q000737:chemistry; D008628:Mercury / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D014269:Trifluoroacetic Acid / Q000737:chemistry*
chemical_list: D006027:Glycosides; D006539:Heptoses; D014269:Trifluoroacetic Acid; D008628:Mercury
keywords: Fleming-Tamao oxidation; Grignard addition; Heptose; Homologation; Lipopolysaccharide