Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 19, Pages 7043-7047Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201406591
Keywords
C-disaccharides; C-glycosides; diastereoselectivity; Mitsunobu reaction; sp(2)-sp(3) coupling
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Funding
- Grant Agency of the Czech Republic [P207/12/P713, 15-17572S]
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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.
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