Hydrolysis of Cyclic Phosphites/Phosphoramidites and Its Inhibition-Reversible Cyclization of Acyclic Phosphonate Salts to Cyclic Phosphites

Organic Process Research and Development

Volumn 7, Issue 6, 2003, Pages 925-928

  Satish Kumar, N ^a   Kumaraswamy, Sudha ^a   Said, Musa A ^a   Kumara Swamy, K C ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

PHENOL; PHOSPHITE; PHOSPHONIC ACID DERIVATIVE; PHOSPHORAMIDITE; PHOSPHORUS DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPETITION; CYCLIZATION; HEATING; HYDROLYSIS;

EID: 0346104833     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op034058k     Document Type: Article

References (34)

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3. Selected references: (a) Zhang, Z.; Wong, C.-H. Glycosylation methods: Use of phosphites. In Carbohydrates in Chemistry and Biology; Ernst, B., Hart, G. W., Sinay, P., Eds.; Wiley-VCH: New York, 2000; p 117. (b) Oka, N.; Wada, T. ; Saigo, K. J. Am. Chem. Soc. 2002, 124, 4962. (c) Wilk, A.; Grajkowski, A.; Phillips, L. R.; Beaucage, S. L. J. Am. Chem. Soc. 2000, 122, 2149. (d) Hayakawa, Y.; Kawai, R.; Hirata, A.; Sugimoto, J.-i.; Kataoka, M.; Sakakura, A. ; Hirose, M.; Noyori, R. J. Am. Chem. Soc. 2001, 123, 8165. (e) Burgess, K.; Cook, D. Chem. Rev. 2000, 100, 2047.
4. Selected references: (a) Zhang, Z.; Wong, C.-H. Glycosylation methods: Use of phosphites. In Carbohydrates in Chemistry and Biology; Ernst, B., Hart, G. W., Sinay, P., Eds.; Wiley-VCH: New York, 2000; p 117. (b) Oka, N.; Wada, T. ; Saigo, K. J. Am. Chem. Soc. 2002, 124, 4962. (c) Wilk, A.; Grajkowski, A.; Phillips, L. R.; Beaucage, S. L. J. Am. Chem. Soc. 2000, 122, 2149. (d) Hayakawa, Y.; Kawai, R.; Hirata, A.; Sugimoto, J.-i.; Kataoka, M.; Sakakura, A. ; Hirose, M.; Noyori, R. J. Am. Chem. Soc. 2001, 123, 8165. (e) Burgess, K.; Cook, D. Chem. Rev. 2000, 100, 2047.
5. Selected references: (a) Zhang, Z.; Wong, C.-H. Glycosylation methods: Use of phosphites. In Carbohydrates in Chemistry and Biology; Ernst, B., Hart, G. W., Sinay, P., Eds.; Wiley-VCH: New York, 2000; p 117. (b) Oka, N.; Wada, T. ; Saigo, K. J. Am. Chem. Soc. 2002, 124, 4962. (c) Wilk, A.; Grajkowski, A.; Phillips, L. R.; Beaucage, S. L. J. Am. Chem. Soc. 2000, 122, 2149. (d) Hayakawa, Y.; Kawai, R.; Hirata, A.; Sugimoto, J.-i.; Kataoka, M.; Sakakura, A. ; Hirose, M.; Noyori, R. J. Am. Chem. Soc. 2001, 123, 8165. (e) Burgess, K.; Cook, D. Chem. Rev. 2000, 100, 2047.
6. Selected references: (a) Zhang, Z.; Wong, C.-H. Glycosylation methods: Use of phosphites. In Carbohydrates in Chemistry and Biology; Ernst, B., Hart, G. W., Sinay, P., Eds.; Wiley-VCH: New York, 2000; p 117. (b) Oka, N.; Wada, T. ; Saigo, K. J. Am. Chem. Soc. 2002, 124, 4962. (c) Wilk, A.; Grajkowski, A.; Phillips, L. R.; Beaucage, S. L. J. Am. Chem. Soc. 2000, 122, 2149. (d) Hayakawa, Y.; Kawai, R.; Hirata, A.; Sugimoto, J.-i.; Kataoka, M.; Sakakura, A. ; Hirose, M.; Noyori, R. J. Am. Chem. Soc. 2001, 123, 8165. (e) Burgess, K.; Cook, D. Chem. Rev. 2000, 100, 2047.
7. (a) Bauer, I.; Körner, S.; Pawelke, B.; Al-Malaika, S.; Habicher, W. D. Polym. Degrad. Stab. 1998, 62, 175.
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12. Selected references on the hydrolysis of phosphate esters: (a) Wroblewski, A. E.; Verkade, J. G. J. Am. Chem. Soc. 1996, 118, 10168. (b) Gerratana, B.; Sowa, G. A.; Cleland, W. W. J. Am. Chem. Soc. 2000, 122, 12615. (c) Torres, R. A.; Bruice, T. C. J. Am. Chem. Soc. 2000, 122, 781. (d) Kluger, R.; Cameron, L. L. J. Am. Chem. Soc. 2002, 124. 3303. (e) Cassano, A. G.; Anderson, V. E.; Harris, M. E. J. Am. Chem. Soc. 2002, 124, 10964. (f) O'Brien, P. J.; Herschlag, D. Biochemistry 2002, 41, 3207. (g) Blasko, A.; Bruice, T. C. Acc. Chem. Res. 1999, 32, 475. (h) Marian, M.; Anges, M. M.; Tomasz, A. M. J. Chem. Soc., Chem. Commun. 1994, 1537. (i) Oivanen, M.; Kuusela, S.; Lonnberg, H. Chem. Rev. 1998, 98, 961-1044.
13. Selected references on the hydrolysis of phosphate esters: (a) Wroblewski, A. E.; Verkade, J. G. J. Am. Chem. Soc. 1996, 118, 10168. (b) Gerratana, B.; Sowa, G. A.; Cleland, W. W. J. Am. Chem. Soc. 2000, 122, 12615. (c) Torres, R. A.; Bruice, T. C. J. Am. Chem. Soc. 2000, 122, 781. (d) Kluger, R.; Cameron, L. L. J. Am. Chem. Soc. 2002, 124. 3303. (e) Cassano, A. G.; Anderson, V. E.; Harris, M. E. J. Am. Chem. Soc. 2002, 124, 10964. (f) O'Brien, P. J.; Herschlag, D. Biochemistry 2002, 41, 3207. (g) Blasko, A.; Bruice, T. C. Acc. Chem. Res. 1999, 32, 475. (h) Marian, M.; Anges, M. M.; Tomasz, A. M. J. Chem. Soc., Chem. Commun. 1994, 1537. (i) Oivanen, M.; Kuusela, S.; Lonnberg, H. Chem. Rev. 1998, 98, 961-1044.
14. Selected references on the hydrolysis of phosphate esters: (a) Wroblewski, A. E.; Verkade, J. G. J. Am. Chem. Soc. 1996, 118, 10168. (b) Gerratana, B.; Sowa, G. A.; Cleland, W. W. J. Am. Chem. Soc. 2000, 122, 12615. (c) Torres, R. A.; Bruice, T. C. J. Am. Chem. Soc. 2000, 122, 781. (d) Kluger, R.; Cameron, L. L. J. Am. Chem. Soc. 2002, 124. 3303. (e) Cassano, A. G.; Anderson, V. E.; Harris, M. E. J. Am. Chem. Soc. 2002, 124, 10964. (f) O'Brien, P. J.; Herschlag, D. Biochemistry 2002, 41, 3207. (g) Blasko, A.; Bruice, T. C. Acc. Chem. Res. 1999, 32, 475. (h) Marian, M.; Anges, M. M.; Tomasz, A. M. J. Chem. Soc., Chem. Commun. 1994, 1537. (i) Oivanen, M.; Kuusela, S.; Lonnberg, H. Chem. Rev. 1998, 98, 961-1044.
15. Selected references on the hydrolysis of phosphate esters: (a) Wroblewski, A. E.; Verkade, J. G. J. Am. Chem. Soc. 1996, 118, 10168. (b) Gerratana, B.; Sowa, G. A.; Cleland, W. W. J. Am. Chem. Soc. 2000, 122, 12615. (c) Torres, R. A.; Bruice, T. C. J. Am. Chem. Soc. 2000, 122, 781. (d) Kluger, R.; Cameron, L. L. J. Am. Chem. Soc. 2002, 124. 3303. (e) Cassano, A. G.; Anderson, V. E.; Harris, M. E. J. Am. Chem. Soc. 2002, 124, 10964. (f) O'Brien, P. J.; Herschlag, D. Biochemistry 2002, 41, 3207. (g) Blasko, A.; Bruice, T. C. Acc. Chem. Res. 1999, 32, 475. (h) Marian, M.; Anges, M. M.; Tomasz, A. M. J. Chem. Soc., Chem. Commun. 1994, 1537. (i) Oivanen, M.; Kuusela, S.; Lonnberg, H. Chem. Rev. 1998, 98, 961-1044.
16. Selected references on the hydrolysis of phosphate esters: (a) Wroblewski, A. E.; Verkade, J. G. J. Am. Chem. Soc. 1996, 118, 10168. (b) Gerratana, B.; Sowa, G. A.; Cleland, W. W. J. Am. Chem. Soc. 2000, 122, 12615. (c) Torres, R. A.; Bruice, T. C. J. Am. Chem. Soc. 2000, 122, 781. (d) Kluger, R.; Cameron, L. L. J. Am. Chem. Soc. 2002, 124. 3303. (e) Cassano, A. G.; Anderson, V. E.; Harris, M. E. J. Am. Chem. Soc. 2002, 124, 10964. (f) O'Brien, P. J.; Herschlag, D. Biochemistry 2002, 41, 3207. (g) Blasko, A.; Bruice, T. C. Acc. Chem. Res. 1999, 32, 475. (h) Marian, M.; Anges, M. M.; Tomasz, A. M. J. Chem. Soc., Chem. Commun. 1994, 1537. (i) Oivanen, M.; Kuusela, S.; Lonnberg, H. Chem. Rev. 1998, 98, 961-1044.
17. Selected references on the hydrolysis of phosphate esters: (a) Wroblewski, A. E.; Verkade, J. G. J. Am. Chem. Soc. 1996, 118, 10168. (b) Gerratana, B.; Sowa, G. A.; Cleland, W. W. J. Am. Chem. Soc. 2000, 122, 12615. (c) Torres, R. A.; Bruice, T. C. J. Am. Chem. Soc. 2000, 122, 781. (d) Kluger, R.; Cameron, L. L. J. Am. Chem. Soc. 2002, 124. 3303. (e) Cassano, A. G.; Anderson, V. E.; Harris, M. E. J. Am. Chem. Soc. 2002, 124, 10964. (f) O'Brien, P. J.; Herschlag, D. Biochemistry 2002, 41, 3207. (g) Blasko, A.; Bruice, T. C. Acc. Chem. Res. 1999, 32, 475. (h) Marian, M.; Anges, M. M.; Tomasz, A. M. J. Chem. Soc., Chem. Commun. 1994, 1537. (i) Oivanen, M.; Kuusela, S.; Lonnberg, H. Chem. Rev. 1998, 98, 961-1044.
18. Selected references on the hydrolysis of phosphate esters: (a) Wroblewski, A. E.; Verkade, J. G. J. Am. Chem. Soc. 1996, 118, 10168. (b) Gerratana, B.; Sowa, G. A.; Cleland, W. W. J. Am. Chem. Soc. 2000, 122, 12615. (c) Torres, R. A.; Bruice, T. C. J. Am. Chem. Soc. 2000, 122, 781. (d) Kluger, R.; Cameron, L. L. J. Am. Chem. Soc. 2002, 124. 3303. (e) Cassano, A. G.; Anderson, V. E.; Harris, M. E. J. Am. Chem. Soc. 2002, 124, 10964. (f) O'Brien, P. J.; Herschlag, D. Biochemistry 2002, 41, 3207. (g) Blasko, A.; Bruice, T. C. Acc. Chem. Res. 1999, 32, 475. (h) Marian, M.; Anges, M. M.; Tomasz, A. M. J. Chem. Soc., Chem. Commun. 1994, 1537. (i) Oivanen, M.; Kuusela, S.; Lonnberg, H. Chem. Rev. 1998, 98, 961-1044.
19. Selected references on the hydrolysis of phosphate esters: (a) Wroblewski, A. E.; Verkade, J. G. J. Am. Chem. Soc. 1996, 118, 10168. (b) Gerratana, B.; Sowa, G. A.; Cleland, W. W. J. Am. Chem. Soc. 2000, 122, 12615. (c) Torres, R. A.; Bruice, T. C. J. Am. Chem. Soc. 2000, 122, 781. (d) Kluger, R.; Cameron, L. L. J. Am. Chem. Soc. 2002, 124. 3303. (e) Cassano, A. G.; Anderson, V. E.; Harris, M. E. J. Am. Chem. Soc. 2002, 124, 10964. (f) O'Brien, P. J.; Herschlag, D. Biochemistry 2002, 41, 3207. (g) Blasko, A.; Bruice, T. C. Acc. Chem. Res. 1999, 32, 475. (h) Marian, M.; Anges, M. M.; Tomasz, A. M. J. Chem. Soc., Chem. Commun. 1994, 1537. (i) Oivanen, M.; Kuusela, S.; Lonnberg, H. Chem. Rev. 1998, 98, 961-1044.
20. Selected references on the hydrolysis of phosphate esters: (a) Wroblewski, A. E.; Verkade, J. G. J. Am. Chem. Soc. 1996, 118, 10168. (b) Gerratana, B.; Sowa, G. A.; Cleland, W. W. J. Am. Chem. Soc. 2000, 122, 12615. (c) Torres, R. A.; Bruice, T. C. J. Am. Chem. Soc. 2000, 122, 781. (d) Kluger, R.; Cameron, L. L. J. Am. Chem. Soc. 2002, 124. 3303. (e) Cassano, A. G.; Anderson, V. E.; Harris, M. E. J. Am. Chem. Soc. 2002, 124, 10964. (f) O'Brien, P. J.; Herschlag, D. Biochemistry 2002, 41, 3207. (g) Blasko, A.; Bruice, T. C. Acc. Chem. Res. 1999, 32, 475. (h) Marian, M.; Anges, M. M.; Tomasz, A. M. J. Chem. Soc., Chem. Commun. 1994, 1537. (i) Oivanen, M.; Kuusela, S.; Lonnberg, H. Chem. Rev. 1998, 98, 961-1044.
21. Goghova, M.; Karvas, M.; Durmis, J. Chem. Pap. 1989, 43, 421.
22. (a) Emsley, J.; Hall, D. Chemistiy of Phosphorus; Harper & Row: London, 1976; p 145.
23. (b) Edmundson, R. S. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Sutherland, I. O., Vol. Ed.; Pergamon: Exeter, 1979; Vol. 2, Chapter 10.3, pp 1189-1231.
24. Said, M. A.; Vijjulatha, M.; Kumara Swamy, K. C. presented in part at the symposium on Modern Trends in Inorganic Chemistry-VI, Hyderabad, August 17-19, 1995. Abstract no. P-36.
25. Compounds 1a and 2a are very well documented; see: (a) Brault, J. F.; Savignac, P. J. Organomet. Chem. 1974, 66, 71. (b) Muthiah, C.; Praveen Kumar, K.; Aruna Mani, C.; Kumara Swamy, K. C. J. Org. Chem. 2000, 65, 3733.
26. Compounds 1a and 2a are very well documented; see: (a) Brault, J. F.; Savignac, P. J. Organomet. Chem. 1974, 66, 71. (b) Muthiah, C.; Praveen Kumar, K.; Aruna Mani, C.; Kumara Swamy, K. C. J. Org. Chem. 2000, 65, 3733.
27. The hydrogen bonds here are only moderately strong. For comparison, see: Kumara Swamy, K. C.; Kumaraswamy, S.; Kommana, P. J. Am. Chem. Soc. 2001, 123, 12642.
28. For more details on analogous derivatives, see: Said, M. A.; Kumara Swamy, K. C.; Veith, M.; Huch, V. J. Chem. Soc., Perkin Trans, 1 1995, 2945.
29. Kumaraswamy, S.; Selvi, R. S.; Kumara Swamy, K. C. Synthesis 1997, 207.
30. Breslow, R. Acc. Chem. Res. 1995, 28, 146.
31. Khorana, H. G. Chemical Biology-Selected Papers of H. G. Khorana; World Scientific: Singapore, 2000; pp 80-95.
32. Muthiah, C.; Praveen Kumar, K.; Aruna Mani, C.; Kumara Swamy, K. C. J. Org. Chem. 2000, 65, 3733.
33. Sheldrick, G. M. SHELX-97; University of Göttingen, 1997.
34. Said, M. A.; Pülm, M.; Herbst-Irmer, R.; Kumara Swamy, K. C. Inorg. Chem. 1997, 36, 2044.