title: Synthesis of novel 2-deoxy-β-benzyl-C-glycosides by highly stereo- and chemoselective hydrogenation of exo-glycals.
abstract: Novel 2-deoxy-β-benzyl-C-glycosides were prepared in good yields and excellent stereoselectivity by a route involving the Wittig reaction of glycosyl phosphonium salts and reduction of exo-glycals as key steps. Hydrogenation of benzyl protected enol ethers was performed with Pd/C(en) as an effective chemoselective catalyst to afford exclusively β anomers.
authors.affiliation: Laboratorio de Estudio de Compuestos Orgánicos (LADECOR), Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata. 47 y 115, (1900) La Plata, Argentina.
authors.forename: Gisela
authors.initials: G
authors.lastname: Díaz
authors.affiliation: Laboratorio de Estudio de Compuestos Orgánicos (LADECOR), Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata. 47 y 115, (1900) La Plata, Argentina. Electronic address: ponzinibbio@quimica.unlp.edu.ar.
authors.forename: Agustín
authors.initials: A
authors.lastname: Ponzinibbio
authors.affiliation: Laboratorio de Estudio de Compuestos Orgánicos (LADECOR), Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata. 47 y 115, (1900) La Plata, Argentina.
authors.forename: Rodolfo Daniel
authors.initials: RD
authors.lastname: Bravo
mesh_terms: D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D006865:Hydrogenation; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D006027:Glycosides
keywords: C-Glycosides; Hydrogenation; Palladium catalyst; Wittig reaction; exo-Glycals