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

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F15%3A00444203" target="_blank" >RIV/61388963:_____/15:00444203 - isvavai.cz</a>
Alternative codes found
RIV/60461373:22330/15:43899483
Result on the web
<a href="http://dx.doi.org/10.1002/chem.201406591" target="_blank" >http://dx.doi.org/10.1002/chem.201406591</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/chem.201406591" target="_blank" >10.1002/chem.201406591</a>

Result language
angličtina
Original language name
Modular Stereoselective Synthesis of (1 -> 2)-C-Glycosides based on the sp(2)-sp(3) Suzuki-Miyaura Reaction
Original language description
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-reductivetransformations. 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.
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2015
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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