title: Modular Stereoselective Synthesis of (1→2)-C-Glycosides based on the sp(2) -sp(3) Suzuki-Miyaura Reaction.
abstract: This work reports a modular and rapid approach to the stereoselective synthesis of a variety of α- and β-(1→2)-linked C-disaccharides. The key step is a Ni-catalyzed cross-coupling reaction of D-glucal pinacol boronate with alkyl halide glycoside easily prepared from commercially available D-glucal. The products of this sp(2) -sp(3) cross-coupling reaction can be converted to glucopyranosyl, mannopyranosyl, or 2-deoxy-glucopyranosyl C-mannopyranosides by one- or two-step stereoselective oxidative-reductive transformations. To the best of our knowledge, we demonstrated the first synthetic application of a challenging sp(2) -sp(3) Suzuki-Miyaura cross-coupling reaction in carbohydrate chemistry.
authors: Department of Chemistry of Natural Compounds, University of Chemistry and Technology, Prague, Technická 5, 166 28 Prague 6 (Czech Republic).
authors: Beata
authors: B
authors: Oroszova
authors: Jan
authors: J
authors: Choutka
authors: Radek
authors: R
authors: Pohl
authors: Kamil
authors: K
authors: Parkan
mesh_terms: D001897:Boronic Acids / Q000138:chemical synthesis / Q000737:chemistry; D003847:Deoxyglucose / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D001897:Boronic Acids; D004187:Disaccharides; D006027:Glycosides; C001289:d-glucal; D003847:Deoxyglucose
keywords: C-disaccharides; C-glycosides; Mitsunobu reaction; diastereoselectivity; sp2-sp3 coupling