title: Synthesis of beta-C-galacto-pyranosides with fluorine on the pseudoanomeric substituent.
abstract: [reaction: see text] beta-C-galacto-Pyranosides with CHF and CF2 substitutes for the glycosidic oxygen were prepared through a four-step sequence starting from a central 1-thio-1,2-O-isopropylidene acetal alcohol and different alpha-fluoro- and alpha,alpha-difluoro acids. The key step in the synthesis is the oxocarbenium cyclization of an intermediate enol ether-thioacetal to a C1-substituted glycal.
authors.affiliation: Department of Chemistry, Hunter College, 695 Park Avenue, New York, New York 10021, USA.
authors.forename: Kurissery A
authors.initials: KA
authors.lastname: Tony
authors.forename: Richard W
authors.initials: RW
authors.lastname: Denton
authors.forename: Anna
authors.initials: A
authors.lastname: Dilhas
authors.forename: Jesús
authors.initials: J
authors.lastname: Jiménez-Barbero
authors.forename: David R
authors.initials: DR
authors.lastname: Mootoo
mesh_terms: D000143:Acids / Q000737:chemistry; D005461:Fluorine / Q000737:chemistry*; D005690:Galactose / Q000138:chemical synthesis / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D000143:Acids; D006027:Glycosides; D005461:Fluorine; D005690:Galactose