Modular Stereoselective Synthesis of (1 -> 2)-C-Glycosides based on the sp(2)-sp(3) Suzuki-Miyaura Reaction

0444203 - ÚOCHB 2016 RIV DE eng J - Článek v odborném periodiku
Oroszová, B. - Choutka, J. - Pohl, Radek - Parkan, K.
Modular Stereoselective Synthesis of (1 -> 2)-C-Glycosides based on the sp(2)-sp(3) Suzuki-Miyaura Reaction.
Chemistry - A European Journal. Roč. 21, č. 19 (2015), s. 7043-7047. ISSN 0947-6539. E-ISSN 1521-3765
Grant ostatní: GA ČR(CZ) GPP207/12/P713; GA ČR(CZ) GA15-17572S
Institucionální podpora: RVO:61388963
Klíčová slova: C-disaccharides * C-glycosides * diastereoselectivity * Mitsunobu reaction * sp(2)-sp(3) coupling
Kód oboru RIV: CC - Organická chemie
Impakt faktor: 5.771, rok: 2015

This work reports a modular and rapid approach to the stereoselective synthesis of a variety of - and -(12)-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.
Trvalý link: http://hdl.handle.net/11104/0246785