Modular Stereoselective Synthesis of (1→2)-C-Glycosides based on the sp(2) -sp(3) Suzuki-Miyaura Reaction
Jazyk angličtina Země Německo Médium print-electronic
Typ dokumentu časopisecké články, práce podpořená grantem
PubMed
25801323
DOI
10.1002/chem.201406591
Knihovny.cz E-zdroje
- Klíčová slova
- C-disaccharides, C-glycosides, Mitsunobu reaction, diastereoselectivity, sp2-sp3 coupling,
- MeSH
- deoxyglukosa analogy a deriváty chemická syntéza chemie MeSH
- disacharidy chemická syntéza chemie MeSH
- glykosidy chemická syntéza chemie MeSH
- kyseliny boronové chemická syntéza chemie MeSH
- oxidace-redukce MeSH
- stereoizomerie MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- d-glucal MeSH Prohlížeč
- deoxyglukosa MeSH
- disacharidy MeSH
- glykosidy MeSH
- kyseliny boronové MeSH
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.
Citace poskytuje Crossref.org
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