Stereoselective Synthesis of C-Glycosides using Potassium Aryltrifluoroborates

Stereoselective Synthesis of C-Glycosides using Potassium Aryltrifluoroborates

Freitas, Juliano C. R.; Santos, Wagner C. C. dos; Silva, Bruna L. da; Menezes, Paulo H.; Oliveira, Roberta A.

Abstract:

O-Glycosidic compounds are the most abundant and important among all types of glycosides, whereas Cglycosides have attracted considerable interest due to their interesting structures and higher stability toward glycosidases and hydrolytic conditions. Organotrifluoroborates have proven to be a good option to replace boronic acids and boronate esters in many reactions involving the formation of a new C-C bond. Herein, we wish to describe the reaction of potassium aryl trifluoroborates and a sugar oxocarbonium ion to promote the direct Cglycosylation.

O-Glycosidic compounds are the most abundant and important among all types of glycosides, whereas Cglycosides have attracted considerable interest due to their interesting structures and higher stability toward glycosidases and hydrolytic conditions. Organotrifluoroborates have proven to be a good option to replace boronic acids and boronate esters in many reactions involving the formation of a new C-C bond. Herein, we wish to describe the reaction of potassium aryl trifluoroborates and a sugar oxocarbonium ion to promote the direct Cglycosylation.

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DOI: 10.5151/chempro-14bmos-R0220-1

Referências bibliográficas

• [1] 1 Vieira, A. S.; Fiorante, P. F.; Hough, T. L. S.; Ferreira, F. P.; Ludtke, D. S.; Stefani, H. A. Org. Lett. 2008, 10, 5215.
• [2] 2 Oliveira, R. A. ; Silva, R. O. ; Molander, G. A. ; Menezes. P. H. Magn. Res. Chem. 2009, 47, 873.

Como citar:

Freitas, Juliano C. R.; Santos, Wagner C. C. dos; Silva, Bruna L. da; Menezes, Paulo H.; Oliveira, Roberta A.; "Stereoselective Synthesis of C-Glycosides using Potassium Aryltrifluoroborates", p-220-220. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0220-1