title: Syntheses of difluorinated carbasugar phosphates from trifluoroethanol.
abstract: Difluorinated cyclohexene diols (prepared from trifluoroethanol) can be elaborated to racemic analogues of phosphorylated sugars via regioselective protection and phosphorylation of the exposed C-1 hydroxyl group. Cis-diol protection was achieved using stannylene methodology, though the regioselectivity depended on the orientation of the methyl group at C-5. UpJohn dihydroxylation is effective with the phosphotriester in place and global deprotection to the tetrol monophosphates is efficient.
authors.affiliation: Department of Chemistry, University of Leicester, University Road, Leicester, LE1 7RH, UK.
authors.forename: Timo
authors.initials: T
authors.lastname: Anderl
authors.forename: Christophe
authors.initials: C
authors.lastname: Audouard
authors.forename: Afjal
authors.initials: A
authors.lastname: Miah
authors.forename: Jonathan M
authors.initials: JM
authors.lastname: Percy
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Rinaudo
authors.forename: Kuldip
authors.initials: K
authors.lastname: Singh
mesh_terms: D054329:Carbasugars / Q000138:chemical synthesis*; D054879:Halogenation; D013403:Sugar Phosphates / Q000138:chemical synthesis*; D014270:Trifluoroethanol / Q000737:chemistry*
chemical_list: D054329:Carbasugars; D013403:Sugar Phosphates; D014270:Trifluoroethanol