SYNTHESIS OF 2,3-UNSATURATED O-GLYCOSIDES MEDIATED BY ULTRASOUND IRRADIATION

SYNTHESIS OF 2,3-UNSATURATED O-GLYCOSIDES MEDIATED BY ULTRASOUND IRRADIATION

Silva, Anderson J. Firmino Santos; Regueira, Juliana L. L. F.; Freitas, Jucleiton José R. de; Freitas, Juliano C. Rufino de; Filho, João R. de Freitas

Abstract:

Lewis acid-catalyzed allylic rearrangement of glycals in the presence of alcohol is well known as the Ferrier reaction and widely employed to obtain the 2,3-unsaturated glycosides. 2,3-Unsaturated-O-glycosides are also important building blocks in the synthesis of some antibiotics. The Ferrier rearrangement involves the intermediacy of an allylic oxycarbenium ion to which the nucleophile adds preferentially in a quasi-axial orientation. The Lewis acid catalysts used for this rearrangement include BF3•OEt2, SnCl4, FeCl3, DDQ, NIS, I2, acidic Montmorillonite K-10, BiCl3, InCl3 , Sc(OTf)3 and Yb(OTf)3, Sc(OTf)3 and Yb(OTf)3 and [Bi(OTf)3]. In recent years have also been employed for the Ferrier rearrangement the tellurium (IV) tetrachloride. In the papar, we set out to explore the potential of p-tolyl sulfonic acid for the preparation of 2,3-unsaturated O-glycosides through Ferrier rearrangement of 3,4,6-tri-O-acetylglucal, mediated by ultrasound irradiation.

Lewis acid-catalyzed allylic rearrangement of glycals in the presence of alcohol is well known as the Ferrier reaction and widely employed to obtain the 2,3-unsaturated glycosides. 2,3-Unsaturated-O-glycosides are also important building blocks in the synthesis of some antibiotics. The Ferrier rearrangement involves the intermediacy of an allylic oxycarbenium ion to which the nucleophile adds preferentially in a quasi-axial orientation. The Lewis acid catalysts used for this rearrangement include BF3•OEt2, SnCl4, FeCl3, DDQ, NIS, I2, acidic Montmorillonite K-10, BiCl3, InCl3 , Sc(OTf)3 and Yb(OTf)3, Sc(OTf)3 and Yb(OTf)3 and [Bi(OTf)3]. In recent years have also been employed for the Ferrier rearrangement the tellurium (IV) tetrachloride. In the papar, we set out to explore the potential of p-tolyl sulfonic acid for the preparation of 2,3-unsaturated O-glycosides through Ferrier rearrangement of 3,4,6-tri-O-acetylglucal, mediated by ultrasound irradiation.

Palavras-chave:

DOI: 10.5151/chempro-15bmos-BMOS2013_2013926103043

Referências bibliográficas

• [1] 1Ferrier, R. J.; Prasad, N. J.Chem. Soc. 1969, 570.
• [2] 2Williams, N. R.; Wander, J. D. The Carbohydrates: Chemistry
• [3] and Biochemistry; Academic Press: New York 1980; 761
• [4] 3Freitas, J. C. R; Couto, T. R.; Paulino, A. A. S.; de Freitas Filho, J. R.;
• [5] Malvestiti, I.; Oliveira, R. A.; Menezes, P. M. Tetrahedron. 2012, 68,
• [6] 10611-10620.
• [7] 4Shostakovskii, M.F.; Annenkova, V.M.; Gaistseva, E.A.; Lavrova, K.F.;
• [8] Polyakov, A.I. Izvest. Sibirsk. Otdel. Akad. Nauk. S.S.S.R., Ser. Khim. Nauk.
• [9] 1967, 163.

Como citar:

Silva, Anderson J. Firmino Santos; Regueira, Juliana L. L. F.; Freitas, Jucleiton José R. de; Freitas, Juliano C. Rufino de; Filho, João R. de Freitas; "SYNTHESIS OF 2,3-UNSATURATED O-GLYCOSIDES MEDIATED BY ULTRASOUND IRRADIATION", p-288-288. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_2013926103043