Synthesis of 2′-O-methoxyethylguanosine using a novel silicon-based protecting group

Journal of Organic Chemistry

Volumn 67, Issue 22, 2002, Pages 7887-7889

  Wen, Ke ^a   Chow, Suetying ^a   Sanghvi, Yogesh S ^b   Theodorakis, Emmanuel A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b ISIS PHARMACEUTICALS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SILYLATION;

ALKYLATION; BIOSYNTHESIS; SILICON; STEREOCHEMISTRY; SUGARS;

AMINO ACIDS;

2' O METHOXYETHYLGUANOSINE; GUANOSINE DERIVATIVE; SILICON; UNCLASSIFIED DRUG; GUANOSINE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; CHEMISTRY;

ALKYLATION; GUANOSINE; MOLECULAR STRUCTURE; SILICON;

EID: 0036827591     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo025970e     Document Type: Article

References (40)

1. Sohail, M. Drug Discuss. Today 2001, 6, 1260-1261. Dean, N. M. Curr. Opin. Biotechnol. 2001, 12, 622-625. Crooke, S. T. Oncogene 2000, 19, 6651-6659. Green, D. W.; Roh, H.; Pippin, J.; Drebin, J. A. J. Am. Coll. Surg. 2000, 191, 93-105. Koller, E.; Gaarde, W. A.; Monia, B. P. Trends Pharmacol. Sci. 2000, 21, 142-148. Sanghvi, Y. S. In Comprehensive Natural Products Chemistry; Barton, D. H. R., Nakanishi, K., Eds.-in-Chief; Vol. 7: DNA and Aspects of Molecular Biology; Kool, E. T., Ed.; Academic Press: New York, 1999; pp 258-311.
2. Sohail, M. Drug Discuss. Today 2001, 6, 1260-1261. Dean, N. M. Curr. Opin. Biotechnol. 2001, 12, 622-625. Crooke, S. T. Oncogene 2000, 19, 6651-6659. Green, D. W.; Roh, H.; Pippin, J.; Drebin, J. A. J. Am. Coll. Surg. 2000, 191, 93-105. Koller, E.; Gaarde, W. A.; Monia, B. P. Trends Pharmacol. Sci. 2000, 21, 142-148. Sanghvi, Y. S. In Comprehensive Natural Products Chemistry; Barton, D. H. R., Nakanishi, K., Eds.-in-Chief; Vol. 7: DNA and Aspects of Molecular Biology; Kool, E. T., Ed.; Academic Press: New York, 1999; pp 258-311.
3. Sohail, M. Drug Discuss. Today 2001, 6, 1260-1261. Dean, N. M. Curr. Opin. Biotechnol. 2001, 12, 622-625. Crooke, S. T. Oncogene 2000, 19, 6651-6659. Green, D. W.; Roh, H.; Pippin, J.; Drebin, J. A. J. Am. Coll. Surg. 2000, 191, 93-105. Koller, E.; Gaarde, W. A.; Monia, B. P. Trends Pharmacol. Sci. 2000, 21, 142-148. Sanghvi, Y. S. In Comprehensive Natural Products Chemistry; Barton, D. H. R., Nakanishi, K., Eds.-in-Chief; Vol. 7: DNA and Aspects of Molecular Biology; Kool, E. T., Ed.; Academic Press: New York, 1999; pp 258-311.
4. Sohail, M. Drug Discuss. Today 2001, 6, 1260-1261. Dean, N. M. Curr. Opin. Biotechnol. 2001, 12, 622-625. Crooke, S. T. Oncogene 2000, 19, 6651-6659. Green, D. W.; Roh, H.; Pippin, J.; Drebin, J. A. J. Am. Coll. Surg. 2000, 191, 93-105. Koller, E.; Gaarde, W. A.; Monia, B. P. Trends Pharmacol. Sci. 2000, 21, 142-148. Sanghvi, Y. S. In Comprehensive Natural Products Chemistry; Barton, D. H. R., Nakanishi, K., Eds.-in-Chief; Vol. 7: DNA and Aspects of Molecular Biology; Kool, E. T., Ed.; Academic Press: New York, 1999; pp 258-311.
5. Sohail, M. Drug Discuss. Today 2001, 6, 1260-1261. Dean, N. M. Curr. Opin. Biotechnol. 2001, 12, 622-625. Crooke, S. T. Oncogene 2000, 19, 6651-6659. Green, D. W.; Roh, H.; Pippin, J.; Drebin, J. A. J. Am. Coll. Surg. 2000, 191, 93-105. Koller, E.; Gaarde, W. A.; Monia, B. P. Trends Pharmacol. Sci. 2000, 21, 142-148. Sanghvi, Y. S. In Comprehensive Natural Products Chemistry; Barton, D. H. R., Nakanishi, K., Eds.-in-Chief; Vol. 7: DNA and Aspects of Molecular Biology; Kool, E. T., Ed.; Academic Press: New York, 1999; pp 258-311.
6. Sohail, M. Drug Discuss. Today 2001, 6, 1260-1261. Dean, N. M. Curr. Opin. Biotechnol. 2001, 12, 622-625. Crooke, S. T. Oncogene 2000, 19, 6651-6659. Green, D. W.; Roh, H.; Pippin, J.; Drebin, J. A. J. Am. Coll. Surg. 2000, 191, 93-105. Koller, E.; Gaarde, W. A.; Monia, B. P. Trends Pharmacol. Sci. 2000, 21, 142-148. Sanghvi, Y. S. In Comprehensive Natural Products Chemistry; Barton, D. H. R., Nakanishi, K., Eds.-in-Chief; Vol. 7: DNA and Aspects of Molecular Biology; Kool, E. T., Ed.; Academic Press: New York, 1999; pp 258-311.
7. Sohail, M. Drug Discuss. Today 2001, 6, 1260-1261. Dean, N. M. Curr. Opin. Biotechnol. 2001, 12, 622-625. Crooke, S. T. Oncogene 2000, 19, 6651-6659. Green, D. W.; Roh, H.; Pippin, J.; Drebin, J. A. J. Am. Coll. Surg. 2000, 191, 93-105. Koller, E.; Gaarde, W. A.; Monia, B. P. Trends Pharmacol. Sci. 2000, 21, 142-148. Sanghvi, Y. S. In Comprehensive Natural Products Chemistry; Barton, D. H. R., Nakanishi, K., Eds.-in-Chief; Vol. 7: DNA and Aspects of Molecular Biology; Kool, E. T., Ed.; Academic Press: New York, 1999; pp 258-311.
8. Antisense Drug Technology Principles, Strategies and Applications; Crooke, S. T., Ed.; Marcel Dekker: New York, 2001.
9. Herdewijin, P. Antisense Nucl. Acid Drug Dev. 2000, 10, 297-310. An, H.; Wang, T.; Maier, M. A.; Manoharan, M.; Ross, B. S.; Cook, P. D. J. Org. Chem. 2001, 66, 2789-2801. Andrade, M.; Scozzari, A. S.; Cole, D. L.; Ravikumar, V. T. Nucleosides Nucleotides 1997, 16, 1617-1620.
10. Herdewijin, P. Antisense Nucl. Acid Drug Dev. 2000, 10, 297-310. An, H.; Wang, T.; Maier, M. A.; Manoharan, M.; Ross, B. S.; Cook, P. D. J. Org. Chem. 2001, 66, 2789-2801. Andrade, M.; Scozzari, A. S.; Cole, D. L.; Ravikumar, V. T. Nucleosides Nucleotides 1997, 16, 1617-1620.
11. Herdewijin, P. Antisense Nucl. Acid Drug Dev. 2000, 10, 297-310. An, H.; Wang, T.; Maier, M. A.; Manoharan, M.; Ross, B. S.; Cook, P. D. J. Org. Chem. 2001, 66, 2789-2801. Andrade, M.; Scozzari, A. S.; Cole, D. L.; Ravikumar, V. T. Nucleosides Nucleotides 1997, 16, 1617-1620.
12. Beigelman, L.; Haeberli, P.; Sweedler, D.; Karpeisky, A. Tetrahedron 2000, 56, 1047-1056. Ross, B. S.; Springer, R. H.; Tortorice, Z.; Dimock, S. Nucleosides Nucleotides 1997, 16, 1641-1643. Chanteloup, L.; Thuong, N. T. Tetrahedron Lett. 1994, 35, 877-880. Roy, S. K.; Tang, J.-Y. Org. Process Res. Devel. 2000, 4, 170-171. Von Matt, P.; Lochmann, T.; Kesselring, R.; Altmann, K.-H. Tetrahedron Lett. 1999, 40, 1873-1876. Beigelman, L.; Sweedler, D.; Haeberli, P.; Karpeisky, A. U.S. Patent No. 5,962,575, 1999.
13. Beigelman, L.; Haeberli, P.; Sweedler, D.; Karpeisky, A. Tetrahedron 2000, 56, 1047-1056. Ross, B. S.; Springer, R. H.; Tortorice, Z.; Dimock, S. Nucleosides Nucleotides 1997, 16, 1641-1643. Chanteloup, L.; Thuong, N. T. Tetrahedron Lett. 1994, 35, 877-880. Roy, S. K.; Tang, J.-Y. Org. Process Res. Devel. 2000, 4, 170-171. Von Matt, P.; Lochmann, T.; Kesselring, R.; Altmann, K.-H. Tetrahedron Lett. 1999, 40, 1873-1876. Beigelman, L.; Sweedler, D.; Haeberli, P.; Karpeisky, A. U.S. Patent No. 5,962,575, 1999.
14. Beigelman, L.; Haeberli, P.; Sweedler, D.; Karpeisky, A. Tetrahedron 2000, 56, 1047-1056. Ross, B. S.; Springer, R. H.; Tortorice, Z.; Dimock, S. Nucleosides Nucleotides 1997, 16, 1641-1643. Chanteloup, L.; Thuong, N. T. Tetrahedron Lett. 1994, 35, 877-880. Roy, S. K.; Tang, J.-Y. Org. Process Res. Devel. 2000, 4, 170-171. Von Matt, P.; Lochmann, T.; Kesselring, R.; Altmann, K.-H. Tetrahedron Lett. 1999, 40, 1873-1876. Beigelman, L.; Sweedler, D.; Haeberli, P.; Karpeisky, A. U.S. Patent No. 5,962,575, 1999.
15. Beigelman, L.; Haeberli, P.; Sweedler, D.; Karpeisky, A. Tetrahedron 2000, 56, 1047-1056. Ross, B. S.; Springer, R. H.; Tortorice, Z.; Dimock, S. Nucleosides Nucleotides 1997, 16, 1641-1643. Chanteloup, L.; Thuong, N. T. Tetrahedron Lett. 1994, 35, 877-880. Roy, S. K.; Tang, J.-Y. Org. Process Res. Devel. 2000, 4, 170-171. Von Matt, P.; Lochmann, T.; Kesselring, R.; Altmann, K.-H. Tetrahedron Lett. 1999, 40, 1873-1876. Beigelman, L.; Sweedler, D.; Haeberli, P.; Karpeisky, A. U.S. Patent No. 5,962,575, 1999.
16. Beigelman, L.; Haeberli, P.; Sweedler, D.; Karpeisky, A. Tetrahedron 2000, 56, 1047-1056. Ross, B. S.; Springer, R. H.; Tortorice, Z.; Dimock, S. Nucleosides Nucleotides 1997, 16, 1641-1643. Chanteloup, L.; Thuong, N. T. Tetrahedron Lett. 1994, 35, 877-880. Roy, S. K.; Tang, J.-Y. Org. Process Res. Devel. 2000, 4, 170-171. Von Matt, P.; Lochmann, T.; Kesselring, R.; Altmann, K.-H. Tetrahedron Lett. 1999, 40, 1873-1876. Beigelman, L.; Sweedler, D.; Haeberli, P.; Karpeisky, A. U.S. Patent No. 5,962,575, 1999.
17. Beigelman, L.; Haeberli, P.; Sweedler, D.; Karpeisky, A. Tetrahedron 2000, 56, 1047-1056. Ross, B. S.; Springer, R. H.; Tortorice, Z.; Dimock, S. Nucleosides Nucleotides 1997, 16, 1641-1643. Chanteloup, L.; Thuong, N. T. Tetrahedron Lett. 1994, 35, 877-880. Roy, S. K.; Tang, J.-Y. Org. Process Res. Devel. 2000, 4, 170-171. Von Matt, P.; Lochmann, T.; Kesselring, R.; Altmann, K.-H. Tetrahedron Lett. 1999, 40, 1873-1876. Beigelman, L.; Sweedler, D.; Haeberli, P.; Karpeisky, A. U.S. Patent No. 5,962,575, 1999.
18. Martin, P. Helv. Chim. Acta 1995, 78, 486-504.
19. Dean, M. N.; Butler, M.; Monia, B. P.; Manoharan, M. In ref 2, pp 319-338. Altmann, K.-H.; Martin, P.; Dean, N. M.; Monia, B. P. Nucleosides Nucleotides 1997, 16, 917-926.
20. Dean, M. N.; Butler, M.; Monia, B. P.; Manoharan, M. In ref 2, pp 319-338. Altmann, K.-H.; Martin, P.; Dean, N. M.; Monia, B. P. Nucleosides Nucleotides 1997, 16, 917-926.
21. The first generation of antisense nucleosides refers to modifications of the phosphodiester backbone by replacing the equatorial oxygen with a sulfur.
22. Legorburu, U.; Reese, C. B.; Song, Q. Tetrahedron 1999, 55, 5635-5640. Altmann, K.-H.; Bevierre, M.-O.; Mesmaeker, A. D.; Moser, H. E. Bioorg. Med. Chem. Lett. 1995, 5, 431-436. Cook, P. D.; Springer, R. H.; Sprankle, K. G.; Ross, B. S. U.S. Patent No. 5,861,493, 1999.
23. Legorburu, U.; Reese, C. B.; Song, Q. Tetrahedron 1999, 55, 5635-5640. Altmann, K.-H.; Bevierre, M.-O.; Mesmaeker, A. D.; Moser, H. E. Bioorg. Med. Chem. Lett. 1995, 5, 431-436. Cook, P. D.; Springer, R. H.; Sprankle, K. G.; Ross, B. S. U.S. Patent No. 5,861,493, 1999.
24. Legorburu, U.; Reese, C. B.; Song, Q. Tetrahedron 1999, 55, 5635-5640. Altmann, K.-H.; Bevierre, M.-O.; Mesmaeker, A. D.; Moser, H. E. Bioorg. Med. Chem. Lett. 1995, 5, 431-436. Cook, P. D.; Springer, R. H.; Sprankle, K. G.; Ross, B. S. U.S. Patent No. 5,861,493, 1999.
25. Grotli, M.; Douglas, M.; Beijer, B.; Garcia, R. G.; Eritja, R.; Sproat, B. J. Chem. Soc., Perkin Trans. 1 1997, 2779-2786. Gundlach, C. W., IV; Ryder, T. R.; Glick, G. D. Tetrahedron Lett. 1997, 38, 4039-4042.
26. Grotli, M.; Douglas, M.; Beijer, B.; Garcia, R. G.; Eritja, R.; Sproat, B. J. Chem. Soc., Perkin Trans. 1 1997, 2779-2786. Gundlach, C. W., IV; Ryder, T. R.; Glick, G. D. Tetrahedron Lett. 1997, 38, 4039-4042.
27. Markiewicz, W. T. J. Chem. Res., Synop. 1979, 24-25. Beijer, B.; Grotli, M.; Douglas, M. E.; Sproat, B. S. Nucleosides Nucleotides 1994, 13, 1905-1927.
28. Markiewicz, W. T. J. Chem. Res., Synop. 1979, 24-25. Beijer, B.; Grotli, M.; Douglas, M. E.; Sproat, B. S. Nucleosides Nucleotides 1994, 13, 1905-1927.
29. Wada, T.; Tobe, M.; Nagayama, T.; Furusawa, K.; Sekine, M. Tetrahedron Lett. 1995, 36, 1683-1684.
30. Grotli, M.; Douglas, M.; Beijer, B.; Eritja, R.; Sproat, B. Bioorg. Med. Chem. Lett. 1997, 7, 425-428.
31. Ferreri, C.; Costantino, C.; Romeo, R.; Chatgilialoglu, C. Tetrahedron Lett. 1999, 40, 1197-1200.
32. The effects of different bases (pyridine, imidazole, triethylamine, and lutidine) and temperature (0-70 °C) for the protection of 5 were investigated. Among them, imidazole was found to produce the best results.
33. Under similar experimental conditions the selective 3′,5′ protection of other nucleic acids with 2 proceeded in 79-92% yield. See the Supporting Information for more details.
34. For the x-ray structure of 6, see the Supporting Information. To the best of our knowledge, this is the first crystal stucture of any 3′,5′-silylated nucleoside.
35. 6-TMS protected alkylated nucleoside (MW = 653) was detected by LCMS analysis of the crude reaction mixture. We thank the reviewer for this suggestion.
36. Zhang, Z.-H.; Li, T.-S.; Yang, F.; Fu, C.-G. Synth. Commun. 1998, 28, 3105-3114. Langer, S. H.; Connell, S.; Wender, I. J. Org. Chem. 1958, 23, 50-57. Sweeley, C. C.; Bentley, R.; Makita, M.; Wells, W. W. J. Am. Chem. Soc. 1963, 85, 2497-2506. Bruynes, C. A.; Jurriens, T. K. J. Org. Chem. 1982, 47, 3966-3969.
37. Zhang, Z.-H.; Li, T.-S.; Yang, F.; Fu, C.-G. Synth. Commun. 1998, 28, 3105-3114. Langer, S. H.; Connell, S.; Wender, I. J. Org. Chem. 1958, 23, 50-57. Sweeley, C. C.; Bentley, R.; Makita, M.; Wells, W. W. J. Am. Chem. Soc. 1963, 85, 2497-2506. Bruynes, C. A.; Jurriens, T. K. J. Org. Chem. 1982, 47, 3966-3969.
38. Zhang, Z.-H.; Li, T.-S.; Yang, F.; Fu, C.-G. Synth. Commun. 1998, 28, 3105-3114. Langer, S. H.; Connell, S.; Wender, I. J. Org. Chem. 1958, 23, 50-57. Sweeley, C. C.; Bentley, R.; Makita, M.; Wells, W. W. J. Am. Chem. Soc. 1963, 85, 2497-2506. Bruynes, C. A.; Jurriens, T. K. J. Org. Chem. 1982, 47, 3966-3969.
39. Zhang, Z.-H.; Li, T.-S.; Yang, F.; Fu, C.-G. Synth. Commun. 1998, 28, 3105-3114. Langer, S. H.; Connell, S.; Wender, I. J. Org. Chem. 1958, 23, 50-57. Sweeley, C. C.; Bentley, R.; Makita, M.; Wells, W. W. J. Am. Chem. Soc. 1963, 85, 2497-2506. Bruynes, C. A.; Jurriens, T. K. J. Org. Chem. 1982, 47, 3966-3969.
40. At present, the mechanism of the desilylation reaction using subequivalent amounts of TBAF is not clear. Our data indicate that in addition to fluoride anion, water is important for this deprotection protocol.