Synthesis of O-Glycosides Dimers Catalysed by Tellurium (IV) Tetrachloride

Synthesis of O-Glycosides Dimers Catalysed by Tellurium (IV) Tetrachloride

Freitas, Juliano C. R.; Couto, Túlio R.; Filho, João R. Freitas; Menezes, Paulo Henrique

Abstract:

The α-2,3-Unsaturated-O-Glycopyranosides are important building blocks in the synthesis of several natural products, glycopeptides, carbohydrate derivatives, oligosaccharides, and nucleosides. The synthesis of this class of compounds is generally based on the glycosidation reaction, which involves a nucleophilic substitution reaction combined with an allylic shift in a glucal. A number of Lewis acids and oxidizing agents can promote the reaction. These methods, however, present some drawbacks such as low yields and lack of selectivity. The ongoing interest in constructing libraries of highly glycosylated compounds that can mimic specific oligosaccharide-protein interactions prompted us to further search for efficient routes based on the use of tellurium tetrahalides toward glycosylated building blocks.

The α-2,3-Unsaturated-O-Glycopyranosides are important building blocks in the synthesis of several natural products, glycopeptides, carbohydrate derivatives, oligosaccharides, and nucleosides. The synthesis of this class of compounds is generally based on the glycosidation reaction, which involves a nucleophilic substitution reaction combined with an allylic shift in a glucal. A number of Lewis acids and oxidizing agents can promote the reaction. These methods, however, present some drawbacks such as low yields and lack of selectivity. The ongoing interest in constructing libraries of highly glycosylated compounds that can mimic specific oligosaccharide-protein interactions prompted us to further search for efficient routes based on the use of tellurium tetrahalides toward glycosylated building blocks.

Palavras-chave:

DOI: 10.5151/chempro-14bmos-R0218-2

Referências bibliográficas

• [1] 1 Chambers, D. J.; Evans, G. R.; Fairbanks, A. J. Tetrahedron: Asymm. 2005, 16, 45–55
• [2] 2 Freitas, J. C. R.; Freitas, J. R.; Menezes. P. H. J. Braz. Chem. Soc. 2010, 21, 2169-2172.

Como citar:

Freitas, Juliano C. R.; Couto, Túlio R.; Filho, João R. Freitas; Menezes, Paulo Henrique; "Synthesis of O-Glycosides Dimers Catalysed by Tellurium (IV) Tetrachloride", p-218-218. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0218-2