First and efficient synthesis of phosphonodifluoromethylene analogues of nucleoside 3′-phosphates: Crucial role played by sulfur in construction of the target molecules

Journal of the American Chemical Society

Volumn 124, Issue 49, 2002, Pages 14668-14675

  Lopin, Chrystel ^a,b   Gautier, Arnaud ^a   Gouhier, Géraldine ^a   Piettre, Serge R ^a  

^a UNIVERSITÉ DE ROUEN   (France)

^b UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; ESTERS; KETONES; LITHIUM COMPOUNDS; SULFUR; SYNTHESIS (CHEMICAL);

STEREOCONTROL;

PHOSPHATES;

BENZOIC ACID DERIVATIVE; FURAN DERIVATIVE; KETONE DERIVATIVE; LITHIUM SALT; NUCLEOSIDE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; SODIUM DERIVATIVE; SULFUR;

ARTICLE; CHEMICAL BOND; DEPROTECTION REACTION; DIASTEREOISOMER; DRUG SYNTHESIS; DRUG TARGETING; OXYGENATION; STEREOCHEMISTRY; SUBSTITUTION REACTION;

HYDROCARBONS, FLUORINATED; NUCLEOTIDES; PHOSPHORIC ACID ESTERS; SULFUR;

EID: 0037065304     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja027850u     Document Type: Article

References (107)

1. (a) Marcusson, E. G.; Yacyshyn, B. R.; Shanahan, W. R., Jr.; Dean, N. M. Mol. Biotechnol. 1999, 12, 1-11.
2. (b) Taylor, J. K.; Dean, N. M. Curr. Opin. Drug Dev. 1999, 2, 147-151.
3. (c) Holmlund, J. T.; Monia, B. P.; Kwoh, T. J.; Dorr, F. A. Curr. Opin. Mol. Ther. 1999, 1. 372-385.
4. (d) Dorr, F. A. Antisense Nucleic Acid Drug Dev. 1999, 9, 391-396.
5. (e) Lebedeva, I. V.; Stein, C. A. BioDrugs 2000, 13, 195-216.
6. (a) De Mesmaeker, A.; Häner, R.; Martin, P.; Moser, H. E. Acc. Chem. Res. 1995, 28, 366-374.
7. (b) Roush, W. Science 1997, 276, 1192-1193.
8. (c) Gee, J. E.; Robbins, I.; van der Laan, A. C.; van Boom, J. H.; Colombier, C.; Leng, M.; Paible, A. M.; Nelson, J. S.; Lebleu, B. Antisense Nucleic Acid Drug Dev. 1998, 8, 103-111.
9. (d) Crooke, S. T. Biochim. Biophys. Acta 1999, 1489, 31-44.
10. (a) Matteucci, M. Perspect. Drug Discovery Des. 1996, 4, 1-16.
11. (b) Gryaznov, S. M.; Skorski, T.; Cucco, C.; Nieborowska-Skorska, M.: Chiu, C. Y.; Lioyd, D.; Chen, J. K.; Kozolkiewicz, M.; Calabretta, B. Nucleic Acids Res. 1996, 24, 1508-1514.
12. (c) Waldner, A.; De Mesmaeker, A.; Wendeborn, S. Bioorg. Med. Chem. Lett. 1996, 6, 2363-2366.
13. (d) Agrawal, S.; Jiang, Z.; Zhao. Q.; Shaw, D.; Cai, Q.; Roskey, A. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 2620-2625.
14. (e) Cook, P. D. Annu. Rep. Med. Chem. 1998, 33, 313-325.
15. (f) Gryaznov, S. M.; Winter, H. Nucleic Acids Res. 1998, 26, 4160-4167.
16. (g) Luo, P.; Leitzel, J. C.; Zhan, Z. Y.; Lynn, D. G. J. Am. Chem. Soc. 1998, 120, 3019-3031.
17. (h) Sergueev, D. S.; Shaw, B. R. J. Am. Chem. Soc. 1998, 120, 9417-9427.
18. (i) Uhlmann, E. Curr. Opin. Drug Discovery Dev. 2000, 3, 203-213.
19. (j) Disney, M. D.; Testa, S. M.; Turner, D. H. Biochemistry 2000, 39, 6991-7000.
20. (k) Sergueeva, Z. A.; Sergueev, D. S.; Ribeiro, A. A.; Summers, J. S.; Shaw, B. R. Helv. Chim. Acta 2000, 83. 1377-1391.
21. Cook, P. D. XIV International Roundtables: Nucleosides, Nucleotides and Their Biological Applications, San Francisco, CA, Sept. 10-14, 2000, No. 34, p 31.
22. (a) Jones, G. H.; Albrechts, H. P.; Damodaran, N. P.; Moffatt, J. G. J. Am. Chem. Soc. 1970, 92, 5510-5511.
23. (b) Albrechts, H. P.; Jones, G. H.; Moffatt, J. G. J. Am. Chem. Soc. 1970, 92, 5511-5513.
24. (c) Morr, M.; Ernst, L.; Grotjahn, L. Z. Naturforsch. 1983, 38b, 1665-1668.
25. (d) Albrechts, H. P.; Jones, G. H.; Moffatt, J. G. Tetrahedron, 1984, 40, 79-85.
26. (e) Morr, M.; Ernst, L.; Schomburg, D. Liebigs Ann. Chem. 1991, 615-631.
27. (f) Serra, C.; Dewynter, G.; Montero, J.-L.; Imbach, J.-L. Tetrathedron 1994, 50, 8427-8444.
28. (g) Lau, W. Y.; Zhang, L.; Wang, J.; Cheng, D.; Zhao, K. Tetrahedron Lett. 1996, 37, 4297-4300.
29. (h) Yokimatsu, T.; Sada, T.; Shimizu, T.; Shibuya, S. Tetrahedron Lett. 1998, 39, 6299-6302.
30. (i) Yokimatsu, T.; Shimizu, T.; Sada, T.; Shibuya, S. Heterocycles 1999, 50, 21-25.
31. (j) An, H.; Wang, T.; Maier, M. A.; Manoharan, M.; Ross, B. S.; Cook, P. D. J. Org. Chem. 2001, 66, 2789-2801.
32. (a) Guschlbauer, W.; Jankowski, K. Nucleic Acids Res. 1991, 6, 521-529.
33. (b) Saenger, W. Principles of Nucleic Acid Structure; Springer-Verlag: New York, Berlin, Heidelberg, Tokyo, 1984.
34. (c) Plaveg, J.; Garg. N.; Chattopadhyaya, J. Chem. Commun. 1993, 1011-1013.
35. (a) Blackburn, G. M.; England, D. A.: Kolmann, F. J. Chem. Soc., Chem. Commun. 1981, 930-932.
36. (b) Blackburn, G. M.; Kent, D. E.; Kolkmann, F. J. Chem. Soc., Chem. Commun. 1981, 1188-1190.
37. (c) McKenna, C. E.; Shen, P.-D. J. Org. Chem. 1981, 46, 4573-4576.
38. (d) Blackburn, G. M.; Kent, D. E. J. Chem. Soc., Perkin Trans 1 1986, 913-917.
39. (e) Phillion, D. P.; Cleary, D. G. J. Org. Chem. 1992, 57, 2763-2764.
40. (f) Burke, T. R., Jr.; Kole, H. K.; Roller, P. P. Biochem. Biophys. Res. Commun. 1994, 204, 129-134.
41. (g) Halazy, S.; Ehrhard, A.; Eggenspiller, A.: Berges-Gross. V.; Danzin, C. Tetrahedron 1996, 52, 177-184.
42. (h) Higashimoto, Y.; Saito, S.; Tong, X.-H.; Hong, A.; Sakaguchi, K.: Appella, E.; Anderson, C. W. J. Biol. Chem. 2000, 275, 23199-23203.
43. It has also been suggested that the α-monofluorophosphonates give, at least in some cases, superior results to αα-difluorination in phosphonate mimics of biological phosphates. See Chambers, R. D.; Jaouhari, R.; O'Hagan, D. Tetrahedron 1989, 45, 5101-5108. (b) Chambers, R. D.; O'Hagan, D.; Lamont, R. B.; Jain, S. C. J. Chem. Soc., Chem. Commun. 1990, 1053-1054. (c) Nieschalk, J.; Batsanov, A. S.; O'Hagan, D.; Howard, J. A. K. Tetrahedron 1996, 52, 165-176. (d) Berkowitz, D. B.; Bose, M.; Pfannenstiel, T. J.; Doukov, T. J. Org. Chem. 2000, 65, 4498-4508. (e) Berkowitz, D. B.; Bose, M. J. Fluorine Chem. 2001. 112, 13-33.
44. It has also been suggested that the α-monofluorophosphonates give, at least in some cases, superior results to αα-difluorination in phosphonate mimics of biological phosphates. See Chambers, R. D.; Jaouhari, R.; O'Hagan, D. Tetrahedron 1989, 45, 5101-5108. (b) Chambers, R. D.; O'Hagan, D.; Lamont, R. B.; Jain, S. C. J. Chem. Soc., Chem. Commun. 1990, 1053-1054. (c) Nieschalk, J.; Batsanov, A. S.; O'Hagan, D.; Howard, J. A. K. Tetrahedron 1996, 52, 165-176. (d) Berkowitz, D. B.; Bose, M.; Pfannenstiel, T. J.; Doukov, T. J. Org. Chem. 2000, 65, 4498-4508. (e) Berkowitz, D. B.; Bose, M. J. Fluorine Chem. 2001. 112, 13-33.
45. It has also been suggested that the α-monofluorophosphonates give, at least in some cases, superior results to αα-difluorination in phosphonate mimics of biological phosphates. See Chambers, R. D.; Jaouhari, R.; O'Hagan, D. Tetrahedron 1989, 45, 5101-5108. (b) Chambers, R. D.; O'Hagan, D.; Lamont, R. B.; Jain, S. C. J. Chem. Soc., Chem. Commun. 1990, 1053-1054. (c) Nieschalk, J.; Batsanov, A. S.; O'Hagan, D.; Howard, J. A. K. Tetrahedron 1996, 52, 165-176. (d) Berkowitz, D. B.; Bose, M.; Pfannenstiel, T. J.; Doukov, T. J. Org. Chem. 2000, 65, 4498-4508. (e) Berkowitz, D. B.; Bose, M. J. Fluorine Chem. 2001. 112, 13-33.
46. It has also been suggested that the α-monofluorophosphonates give, at least in some cases, superior results to αα-difluorination in phosphonate mimics of biological phosphates. See Chambers, R. D.; Jaouhari, R.; O'Hagan, D. Tetrahedron 1989, 45, 5101-5108. (b) Chambers, R. D.; O'Hagan, D.; Lamont, R. B.; Jain, S. C. J. Chem. Soc., Chem. Commun. 1990, 1053-1054. (c) Nieschalk, J.; Batsanov, A. S.; O'Hagan, D.; Howard, J. A. K. Tetrahedron 1996, 52, 165-176. (d) Berkowitz, D. B.; Bose, M.; Pfannenstiel, T. J.; Doukov, T. J. Org. Chem. 2000, 65, 4498-4508. (e) Berkowitz, D. B.; Bose, M. J. Fluorine Chem. 2001. 112, 13-33.
47. It has also been suggested that the α-monofluorophosphonates give, at least in some cases, superior results to αα-difluorination in phosphonate mimics of biological phosphates. See Chambers, R. D.; Jaouhari, R.; O'Hagan, D. Tetrahedron 1989, 45, 5101-5108. (b) Chambers, R. D.; O'Hagan, D.; Lamont, R. B.; Jain, S. C. J. Chem. Soc., Chem. Commun. 1990, 1053-1054. (c) Nieschalk, J.; Batsanov, A. S.; O'Hagan, D.; Howard, J. A. K. Tetrahedron 1996, 52, 165-176. (d) Berkowitz, D. B.; Bose, M.; Pfannenstiel, T. J.; Doukov, T. J. Org. Chem. 2000, 65, 4498-4508. (e) Berkowitz, D. B.; Bose, M. J. Fluorine Chem. 2001. 112, 13-33.
48. (a) Matulic-Adamic, J.; Usman, N. Tetrahedron Lett. 1994, 35, 3227-3230.
49. (b) Matulic-Adamic, J.; Haeberli, P.; Usman, N. J. Org. Chem. 1995. 60, 2563-2569.
50. For example, the lithium salt of dialkyl difluoromethylphosphonates does not react with secondary halides or trifiates. See Obayashi, M.; Ito, E.: Kondo, K. Tetrahedron Lett. 1982, 23, 2323-2326.
51. (a) Piettre, S. R. Tetrahedron Lett. 1996, 37, 2233-2236.
52. (b) Herpin, T. F.; Houlton, J. S.; Motherwell, W. B.; Roberts, B. P.; Weibel, J.-M. J. Chem. Soc., Chem. Commun. 1996, 613-614.
53. (c) Herpin, T. F.; Motherwell, W. B.; Roberts, B. P.; Roland, S.; Weibel, J.-M. Tetrahedron 1997, 53, 15085-15100.
54. (d) Kovensky, J.; McNeil, M.; Sinay, P. J. Org. Chem. 1999. 64, 6202-6205.
55. (e) Berkowitz, D. B.; Eggen, M.; Shen, Q.; Shoemaker, R. K. J. Org. Chem. 1996, 61, 4666-4675.
56. (a) Sabol, J. S.; McCarthy, J. R. Tetrahedron Lett. 1992. 33, 3101-3104.
57. (b) Serafinowski, P. J.; Barnes, C. L. Synthesis 1997, 225-228.
58. (a) Rees, R. D.; James, K.; Tatchell, A. R.; Williams, R. H. J. Chem. Soc. C 1968, 2716-2721.
59. (b) Sowa, W. Can. J. Chem. 1968, 46, 1586-1589.
60. (c) Bourgeois, J. M. Helv. Chim. Acta 1975, 53, 363-372.
61. (d) Yoshimura, J. Adv. Carbohydr. Chem. Biochem. 1984, 42, 69-134.
62. (e) Giese, B.; Gonzälez-Gomez, J. A.; Witzel, T. Angew. Chem., Int. Ed. Engl. 1984, 23, 69-70.
63. (f) Giese, B. Angew. Chem., Int. Ed. Engl. 1989, 28, 969-980.
64. (g) Schmit, C. Synlett 1994, 241-242.
65. (h) Johnson, C. R.; Bhumralkar, D. R.; De Clercq, E. Nucleosides Nucleotides 1995, 14, 185-194.
66. (i) Lavaire, S.; Plantier-Royon, R.; Portella C. J. Carbohydr. Chem. 1996, 15, 361-370.
67. (j) Lavaire, S.; Plantier-Royon, R.; Portella, C. Tetrahedron: Asymmetry 1998, 9, 213-226.
68. (k) Lopin, C.; Gautier, A.; Gouhier, G.; Piettre, S. R. Tetrahedron Lett. 2000. 41. 10195-10200.
69. (l) Gautier, A.; Garipova, G.; Dubert, O.; Oulyadi, H.; Piettre, S. R. Tetrahedron Lett. 2001, 42. 5673-5676.
70. (m) Dubert, O.; Gautier, A.; Condamine, E.; Piettre, S. R. Org. Lett. 2002, 4, 359-362.
71. Prepared by the action of the Dess-Martin reagent on the corresponding alcohol. See Supporting Information.
72. Serafinowski, P. J.; Barnes, C. L. Tetrahedron 1996, 52, 7929-7938.
73. 2. Tri-n-butyltin hydride and tris(trimethylsilyl)silane were used. as hydrogen quenchers in the case of 24c and 24d.
74. (a) Piettre, S. R.; Raboisson, P. Tetrahedron Lett. 1996, 37, 2229-2232.
75. (b) Waschbüsch, R.; Samadi, M.: Savignac, P. J. Organomet. Chem. 1997, 529, 267-278.
76. This was achieved by using standard, published procedures. See Murray, H. D.; Prokop, J. In Synthetic Procedures in Nucleic Acid Chemistry; Zorbach, W. W., Tipson, R. S., Eds.; Wiley-Interscience: New York, 1968; p. 193. (b) Xie, M.; Berges, D. A.; Robins, M. J. J. Org. Chem. 1996, 61, 5178-5179.
77. This was achieved by using standard, published procedures. See Murray, H. D.; Prokop, J. In Synthetic Procedures in Nucleic Acid Chemistry; Zorbach, W. W., Tipson, R. S., Eds.; Wiley-Interscience: New York, 1968; p. 193. (b) Xie, M.; Berges, D. A.; Robins, M. J. J. Org. Chem. 1996, 61, 5178-5179.
78. The literature reports a few cases in which complete selectivity was not observed during acetolysis of an 1,2-acetonide moiety, despite the formation of a 2-acetoxy unit. The suggestion by Shibuya of the possible participation of a phosphonothioyl unit (the resultant of the longer P=S bond, when compared to the P=O bond) might be extended to the difluorinated analogue. See ref 5h.
79. Bozo, E.; Boros, S.; Kuszmann, J.; Gacs-Baitz, E.; Parkanyi, L. Carbohydrate Res. 1998, 308, 297-310.
80. (a) Niedballa, U.; Vorbrüggen, H. Angew. Chem., Int. Ed. Engl. 1970, 9, 461-462.
81. (b) Niedballa, U.; Vorbrüggen, H. J. Org. Chem. 1974, 39, 3654-3660.
82. (c) Ibid., 3660-3663.
83. (d) Ibid., 3664-3667.
84. (e) Ibid., 3668-3671.
85. (f) Ibid., 3672-3674.
86. (g) Niedballa, U.; Vorbrüggen, H. J. Org. Chem. 1976, 41, 2084-2086.
87. (h) Vorbrüggen, H.; Bennua, B. Tetrahedron Lett. 1978, 39, 13391342.
88. (i) Vorbrüggen, H.; Krolikiewicz, K.; Bennua, B. Chem. Ber. 1981, 114, 1234-1255.
89. (j) Vorbrüggen, H.; Hölfe, G. Chem. Ber. 1981, 114, 1256-1268.
90. (a) Saneyoshi, M.; Satoh, E. Chem. Pharm. Bull. 1978, 27, 2518.
91. (b) Zou, R.; Robins, M. J. Can. J. Chem., 1987, 65, 1436-1437.
92. (c) Robins, M. J.; Zou, R.; Guo, Z.; Wnuk, S. F. J. Org. Chem. 1996, 61, 9207-9212.
93. (a) Dudycz, L. W.; Wright, G. E. Nucleosides Nucleotides 1984, 3, 33-44.
94. (b) Wright, G. E.; Dudycz, L. W. J. Med. Chem. 1984, 27, 175-181.
95. (c) Poopeiko, N. E.; Kvasyuk, I. A.; Mikhailopulo, I. A. Synthesis 1985, 605-609.
96. (d) Garner, P.; Ramakanth, S. J. Org. Chem. 1988, 53, 1294-1298.
97. (e) Sheppard, T. L.; Rosenblatt, A. T.; Breslow, R. J. Org. Chem. 1994, 59, 7243-7248.
98. (f) Gosselin, G.; Bergogne, M.-C.; Imbach, J.-L. J. Heterocyclic Chem. 1993, 30, 1229-1233.
99. Piettre, S. R. Tetrahedron Lett. 1996, 37, 4707-4710.
100. Despite the possible oxidation of the base nuclei by m-CPBA (see Tanaka, T.; Letsinger, R. L. Nucleic Acid Res. 1982, 10, 3249-3260), the reactions were found to be very clean.
101. (a) McKenna, C. E.; Higa, M. T.; Cheug, N. H.; McKenna, M. Tetrahedron Lett. 1977, 155.
102. (b) Morita, T.; Okamoto, Y.; Sakurai, H. Bull. Chem. Soc. Jpn. 1978, 51. 2169-2170.
103. (c) Blackburn, G. M.; Kent, D. E. J. Chem. Soc., Chem. Commun. 1981, 511-513.
104. (d) Chambers, R. D.; Jaouhari, R.; O'Hagan, D. Tetrahedron 1989, 45, 5101-5108.
105. (e) Levy, S. G.; Wasson, B,; Carson, D. A.; Cottam, H. B. Synthesis 1996, 843-846.
106. (f) Yokomatsu, T.: Yamagishi, T.; Suemune, K.; Abe, H.; Kihara, T.; Soeda, S.; Shimeno, H.; Shibuya, S. Tetrahedron 2000, 56, 7099-7108.
107. Robins, M. J.; Zou, R.; Guo, Z.; Wnuk, S. F. J. Org. Chem. 1996, 61, 9207-9212.