Direct synthesis of C-glycosides from unprotected 2-N-acyl-aldohexoses via aldol condensation-oxa-Michael reactions with unactivated ketones
Organic and Biomolecular Chemistry, ISSN: 1477-0520, Vol: 14, Issue: 1, Page: 259-264
2015
- 18Citations
- 11Captures
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Article Description
C-glycosides are important compounds as they are used as bioactive molecules and building blocks. We have developed methods to concisely synthesize C-glycosides from unprotected 2-N-acyl-aldohexoses and unactivated ketones; we designed aldol-condensation-oxa-Michael addition reactions catalyzed by amine-based catalysts using additives. Depending on the conditions used, C-glycosides were stereoselectively obtained. Our methods allowed the C-C bond formations at the anomeric centers of unprotected carbohydrates under mild conditions to lead the C-glycosides in atom- and step-economical ways.
Bibliographic Details
http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=84951291867&origin=inward; http://dx.doi.org/10.1039/c5ob02094h; http://www.ncbi.nlm.nih.gov/pubmed/26565955; http://xlink.rsc.org/?DOI=C5OB02094H; http://pubs.rsc.org/en/content/articlepdf/2016/OB/C5OB02094H; https://xlink.rsc.org/?DOI=C5OB02094H; https://dx.doi.org/10.1039/c5ob02094h; https://pubs.rsc.org/en/content/articlelanding/2016/ob/c5ob02094h
Royal Society of Chemistry (RSC)
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