Ultrasonic-Assisted Deprotection of tert-Butyldimethylsilyl Ethers with Bromotrichloromethane in Methanol

Article Preview

Abstract:

Treatment of tert-butyldimethylsilyl (TBDMS) ethers of nucleosides with bromo-trichloromethane (CBrCl3) in methanol under ultrasonic conditions provides a mild and efficient method for desilylation. The experimental results showed that the employment of ultrasonic could notably improve the reaction efficiency compared with thermal heating condition.

You might also be interested in these eBooks

Info:

Periodical:

Pages:

230-233

Citation:

Online since:

October 2013

Export:

Price:

Permissions CCC:

Permissions PLS:

Сopyright:

© 2014 Trans Tech Publications Ltd. All Rights Reserved

Share:

Citation:

* - Corresponding Author

[1] E.J. Corey, A. Venkateswarlu, J. Am. Chem. Soc., Vol. 94 (1972), p.6190.

Google Scholar

[2] E.J. Corey, B. B. Snider, J. Am. Chem. Soc., Vol. 94 (1972), p.2549.

Google Scholar

[3] A.R. Vaino, W. A. Szarek, Chem, Commun., (1996), p.2351.

Google Scholar

[4] A.H. Haines, Adv. Carbohydr. Chem. Biochem., Vol. 33 (1976), p.11.

Google Scholar

[5] R. Baker, W.J. Cummings, J.F. Hayes, and A. Kumar, J. Chem. Soc., Chem. Commun., (1986), p.1237.

Google Scholar

[6] F.T. Liang, N. Jain, T. Hutchens, D.D. Shock, W.A. Beard, S.H. Wilson, M.P. Chiarelli, B.P. Cho, J. Med. Chem., Vol. 51 (2008), p.6460.

Google Scholar

[7] X.F. Zhu, N.H.J. Williams, A.I. Scott, J. Chem. Soc., Perkin Trans., Vol. 1 (2000), p.2305.

Google Scholar

[8] R.V. Somu, D.J. Wilson, E.M. Bennett, H.I. Boshoff, L. Celia, B.J. Beck, C.E. Barry, C.C. Aldrich, J. Med. Chem., Vol. 49 (2006), p.7623.

DOI: 10.1021/jm061068d

Google Scholar

[9] L.L.H. de Fallois, J.L. Decout, M. Fontecave, Tetrahedron Lett., Vol. 36 (1995), p.9479.

Google Scholar

[10] J.H. Cho, S.J. Coats, R.F. Schinazi, Org. Lett., Vol. 14 (2012), p.2488.

Google Scholar

[11] A.S.Y. Lee, H.C. Yeh, M.H. Tsai, Tetrahedron Lett., Vol. 36 (1995), p.6891.

Google Scholar

[12] A.S.Y. Lee, H.C. Yeh, J.J. Shie, Tetrahedron Lett., Vol. 39 (1998), p.5249.

Google Scholar

[13] M.Y. Chen, K.C. Lu, A.S. Y. Lee, C.C. Lin, Tetrahedron Lett., Vol. 43 (2002), p.2777.

Google Scholar

[14] R.R. Koch, E.A. Glende Jr., R.O. Recknagel, Bio. Pharma., Vol. 23 (1974), p.2907.

Google Scholar

[15] B.A. Mico, R.V. Branchflower, L.R. Pohl, A.T. Pudzianowski, G.H. Loew, Life Sci., Vol. 30 (1982), p.131.

Google Scholar