Functionalization of 3,4,6-Tri-O-acetyl-D-Glucal with potassium organotrifluoroborate salts: Synthesis of 1,2,3-triazoles

Functionalization of 3,4,6-Tri-O-acetyl-D-Glucal with potassium organotrifluoroborate salts: Synthesis of 1,2,3-triazoles

Silva, Nathália C. S.; Manarin, Flávia G.; Stefani, Hélio A.; Lüdtke2., Diogo S.

Abstract:

C-glycosides are compounds of extreme interest because they occur in products with relevant biological properties. Moreover, they are interesting synthetic building blocks for further functionalizations. In this context, the use of potassium organotrifluoroborates salts represent an interesting strategy for the synthesis of unsaturated pyranoside derivatives. The goal of this work is the functionalization of a derivative of D-glucose by Ferrier rearrangement, and then the preparation of 1,2,3-triazoles, obtaining products with great structural diversity.

C-glycosides are compounds of extreme interest because they occur in products with relevant biological properties. Moreover, they are interesting synthetic building blocks for further functionalizations. In this context, the use of potassium organotrifluoroborates salts represent an interesting strategy for the synthesis of unsaturated pyranoside derivatives. The goal of this work is the functionalization of a derivative of D-glucose by Ferrier rearrangement, and then the preparation of 1,2,3-triazoles, obtaining products with great structural diversity.

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DOI: 10.5151/chempro-14bmos-R0349-1

Referências bibliográficas

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• [3] 3a)Yeager, A. R.; Min, G. K.; Porco Jr., J. A.; Schaus, S. E. Org. Lett. 2006, 8, 5065.b)Lubin-Germain, N.; Hallonet, A.; Huguenol, F.; Palmier, S.; Uziel, J.; Augé, J. Org. Lett. 2007, 9, 3679.
• [4] 4 Vieira, A. S.; Fiorante, P. F.; Hough, T. L. S.; Ferreira, F. P.; Lüdtke, D. S.; Stefani, H. A. Org. Lett. 2008, 10, 5215.

Como citar:

Silva, Nathália C. S.; Manarin, Flávia G.; Stefani, Hélio A.; Lüdtke2., Diogo S.; "Functionalization of 3,4,6-Tri-O-acetyl-D-Glucal with potassium organotrifluoroborate salts: Synthesis of 1,2,3-triazoles", p-349-349. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0349-1