Setembro 2013 vol. 1 num. 1 - Brazilian Meeting on Organic Synthesis 2011

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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.

Abstract:

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Palavras-chave: O-glycosidation, O-glycoside dimers, tellurium tetrachloride,

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, 2169-217
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 . In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 2318-4043, DOI 10.5151/chempro-14bmos-R0218-2

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