Copyright (c) 2016 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
A Facile Synthesis of 8-Bromo-3-methyl-7-(b-D-ribofuranosyl)purine-2,6-dione with SnCl4 under Vorbruggen Glycosylation Conditions
Corresponding Author(s) : Srujana Suneel Kumar Madana
Asian Journal of Chemistry,
Vol. 28 No. 2 (2016): Vol 28 Issue 2
Abstract
In course of the synthetic studies of 8-bromo-3-methyl based nucleosides, we have developed a high regeo selective synthetic route to acquire N-7 isomer in the presence of different Lewis acids. The glycosylation reaction was performed with tin(IV) chloride as a Lewis acid instead of TMSOTf to avoid the emulsion formation, cross contamination of trifluoromethanesulfonic acid (TfOH) in the isolated product with similar yields (70 %). The concentration of sodium methoxide solution, reaction time and reaction temperature was studied for the successful deprotection of sugars. The consistent heavy metal (tin) lower limit in the range of 10-15 ppm obtained at various scales in isolated nucleosides, which can be pharmaceutically accepted as per ICH guidelines.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- B.G. Ugarkar, A.J. Castellino, J.M. Da Re, J.J. Kopcho, J.B. Wiesner, J.M. Schanzer and M.D. Erion, J. Med. Chem., 43, 2894 (2000); doi:10.1021/jm0000259.
- J.D. Anderson, R.J. Bontems, S. Geary, H.B. Cottam, S.B. Larson, S.S. Matsumoto, D.F. Smee and R.K. Robins, Nucleosides Nucleotides, 8, 1201 (1989); doi:10.1080/07328318908054327.
- H. Vorbruggen and C. Ruh-Pohlenz, Org. React., 55, 1 (2000).
- Z. Kazimierczuk, H.B. Cottam, G.R. Revankar and R.K. Robins, J. Am. Chem. Soc., 106, 6379 (1984); doi:10.1021/ja00333a046.
- (a) H. Vorbruggen and B. Bennua, Tetrahedron Lett., 19, 1339 (1978); doi:10.1016/0040-4039(78)80123-3; (b) H. Vorbruggen and B. Bennua, Chem. Ber., 114, 1279 (1981); doi:10.1002/cber.19811140407; (c) E. Diekmann, K. Friedrich and H.G. Fritz, J. Prakt. Chem., 335, 415 (1993); doi:10.1002/prac.19933350504.
- a) D. Kikelj, N. Ramzaeva, H. Rosemeyer, E. Schaumann, F. Seela and U. Urleb, Hetarenes III (Six-Membered Rings and Larger Hetero-Rings with Maximum Unsaturation) - Part 2b; In: Houben-Weyl Methods of Organic Chemistry (2014); b) E. Fischer and B. Helferich, Ber. Dtsch. Chem. Ges., 47, 210 (1914); doi:10.1002/cber.19140470133; c) O.R. Martin, Tetrahedron Lett., 26, 2055 (1985); doi:10.1016/S0040-4039(00)94777-4; (d) S.H. Langer, S. Connell and I. Wender, Org. Chem., 23, 50 (1958); doi:10.1021/jo01095a017.
- K.Y. Jong, K.S. Ho and B.K. Kim, Tetrahedron Lett., 54, 5484 (2003); doi:10.1016/j.tetlet.2013.07.132.
- H. Vorbruggen, Silicon Mediated Transformations of Functional Groups, John Wiley & Sons, pp. 131-145 (2006).
- B.G. Huang and M. Bobek, Carbohydr. Res., 308, 319 (1998); doi:10.1016/S0008-6215(98)00098-6.
- S. Janardhanam and K.P. Nambiar, Tetrahedron Lett., 35, 3657 (1994); doi:10.1016/S0040-4039(00)73064-4.
- R.F. Lambert, R.J. Hinkle, S.E. Ammann, Y. Lian, J. Liu, S.E. Lewis and R.D. Pike, J. Org. Chem., 76, 9269 (2011); doi:10.1021/jo201478d.
- R. Bookser and B.K. Raffaele, J. Org. Chem., 72, 173 (2007); doi:10.1021/jo061885l.
- R. Ionescu and P. Blumbergs, US Patent 7038038 (2006).
- C. Praveen and V. Satyanarayana, WO Patent 014883, (2010).
- (a) P.T. Jorgensen, E.B. Pedersen and C. Nielsen, Synthesis, 1299 (1992); doi:10.1055/s-1992-26363.; (b) A.A. El-Barbary, A.I. Khodair and E.B. Pedersen, J. Org. Chem., 12, 737 (1993).
References
B.G. Ugarkar, A.J. Castellino, J.M. Da Re, J.J. Kopcho, J.B. Wiesner, J.M. Schanzer and M.D. Erion, J. Med. Chem., 43, 2894 (2000); doi:10.1021/jm0000259.
J.D. Anderson, R.J. Bontems, S. Geary, H.B. Cottam, S.B. Larson, S.S. Matsumoto, D.F. Smee and R.K. Robins, Nucleosides Nucleotides, 8, 1201 (1989); doi:10.1080/07328318908054327.
H. Vorbruggen and C. Ruh-Pohlenz, Org. React., 55, 1 (2000).
Z. Kazimierczuk, H.B. Cottam, G.R. Revankar and R.K. Robins, J. Am. Chem. Soc., 106, 6379 (1984); doi:10.1021/ja00333a046.
(a) H. Vorbruggen and B. Bennua, Tetrahedron Lett., 19, 1339 (1978); doi:10.1016/0040-4039(78)80123-3; (b) H. Vorbruggen and B. Bennua, Chem. Ber., 114, 1279 (1981); doi:10.1002/cber.19811140407; (c) E. Diekmann, K. Friedrich and H.G. Fritz, J. Prakt. Chem., 335, 415 (1993); doi:10.1002/prac.19933350504.
a) D. Kikelj, N. Ramzaeva, H. Rosemeyer, E. Schaumann, F. Seela and U. Urleb, Hetarenes III (Six-Membered Rings and Larger Hetero-Rings with Maximum Unsaturation) - Part 2b; In: Houben-Weyl Methods of Organic Chemistry (2014); b) E. Fischer and B. Helferich, Ber. Dtsch. Chem. Ges., 47, 210 (1914); doi:10.1002/cber.19140470133; c) O.R. Martin, Tetrahedron Lett., 26, 2055 (1985); doi:10.1016/S0040-4039(00)94777-4; (d) S.H. Langer, S. Connell and I. Wender, Org. Chem., 23, 50 (1958); doi:10.1021/jo01095a017.
K.Y. Jong, K.S. Ho and B.K. Kim, Tetrahedron Lett., 54, 5484 (2003); doi:10.1016/j.tetlet.2013.07.132.
H. Vorbruggen, Silicon Mediated Transformations of Functional Groups, John Wiley & Sons, pp. 131-145 (2006).
B.G. Huang and M. Bobek, Carbohydr. Res., 308, 319 (1998); doi:10.1016/S0008-6215(98)00098-6.
S. Janardhanam and K.P. Nambiar, Tetrahedron Lett., 35, 3657 (1994); doi:10.1016/S0040-4039(00)73064-4.
R.F. Lambert, R.J. Hinkle, S.E. Ammann, Y. Lian, J. Liu, S.E. Lewis and R.D. Pike, J. Org. Chem., 76, 9269 (2011); doi:10.1021/jo201478d.
R. Bookser and B.K. Raffaele, J. Org. Chem., 72, 173 (2007); doi:10.1021/jo061885l.
R. Ionescu and P. Blumbergs, US Patent 7038038 (2006).
C. Praveen and V. Satyanarayana, WO Patent 014883, (2010).
(a) P.T. Jorgensen, E.B. Pedersen and C. Nielsen, Synthesis, 1299 (1992); doi:10.1055/s-1992-26363.; (b) A.A. El-Barbary, A.I. Khodair and E.B. Pedersen, J. Org. Chem., 12, 737 (1993).