title: Optimized Synthesis of a Pentafluoro-gem-diol and Conversion to aCF2Br-Glucopyranose through Trifluoroacetate-Release and Halogenation.
abstract: Pentafluoro-gem-diols are substrates that enable the synthesis of valuable difluoromethylene-containing organic molecules through the release of trifluoroacetate. Currently, only one synthetic strategy is available to assemble these important precursors. Herein, two new synthetic strategies to a complex pentafluoro-gem-diol are compared to the existing route, and an improved synthetic route has completed. Moreover, the first synthesis of aCF2Br-glucopyranose was finished by a tandem trifluoroacetate-release halogenation/cyclization protocol.
authors.affiliation: Department of Chemistry, Purdue University, West Lafayette, Indiana, 47907, USA; Department of BioMolecular Sciences, University of Mississippi, Mississippi, 38677, USA.
authors.forename: Robert A
authors.initials: RA
authors.lastname: Hazlitt
authors.affiliation: Department of Chemistry, Purdue University, West Lafayette, Indiana, 47907, USA.
authors.forename: Jinu P
authors.initials: JP
authors.lastname: John
authors.affiliation: Department of BioMolecular Sciences, University of Mississippi, Mississippi, 38677, USA.
authors.forename: Que-Lynn
authors.initials: QL
authors.lastname: Tran
authors.affiliation: Department of Chemistry, Purdue University, West Lafayette, Indiana, 47907, USA; Department of BioMolecular Sciences, University of Mississippi, Mississippi, 38677, USA.
authors.forename: David A
authors.initials: DA
authors.lastname: Colby
keywords: aldol reaction; fluorine; glycoside; halogenation; pyranose