title: Preparation ofC-arylglycals via Suzuki-Miyaura cross-coupling of dihydropyranylphosphates.
abstract: The preparation ofC-arylglycals has been accomplished employing the Suzuki-Miyaura cross-coupling reaction of dihydropyranylphosphates with arylboronate esters. The reaction is tolerant of both electron-donating (EDG) and electron-withdrawing (EWG) groups on the aromatic ring and affords the correspondingC-arylglycals in good to excellent yields (68-97%). Additionally, the ketene acetal phosphate derived from 6-deoxy-3,4-di-O-benzyl-L-rhamnal also couples efficiently to yieldC-arylglycals in excellent yields.
authors.affiliation: Department of Chemistry, Sewanee: The University of the South, 735 University Avenue, Sewanee, TN 37383-1000, USA.
authors.forename: Michelle R
authors.initials: MR
authors.lastname: Leidy
authors.affiliation: Department of Chemistry, Sewanee: The University of the South, 735 University Avenue, Sewanee, TN 37383-1000, USA.
authors.forename: J Mason
authors.initials: JM
authors.lastname: Hoffman
authors.affiliation: Department of Chemistry, Sewanee: The University of the South, 735 University Avenue, Sewanee, TN 37383-1000, USA.
authors.forename: Rongson
authors.initials: R
authors.lastname: Pongdee
keywords: Suzuki-Miyaura; carbohydrates; deoxysugars; glycosides; natural products