Second-generation synthesis of protected phosphonothiodifluoromethylene analogues of nucleoside-3′-phosphates

Tetrahedron

Volumn 60, Issue 22, 2004, Pages 4895-4900

  Kalinina, Irina ^a   Gautier, Arnaud ^a   Salcedo, Carmen ^a   Valnot, Jean Yves ^a   Piettre, Serge R ^a  

^a UNIVERSITÉ DE ROUEN   (France)

Author keywords

Nucleotide analogue; Organomagnesium reagent; Phosphonothiodifluoromethylene

Indexed keywords

1 N [2 O ACETYL 5 (4 CHLOROBENZOYL) 3 DEOXY 3 (O,O DIETHYLPHOSPHONOTHIO)DIFLUOROMETHYL BETA DEXTRO RIBOFURANOSYL]URIDINE; 3 (O,O DIETHYLPHOSPHONOTHIO)DIFLUOROMETHYL 1,2 O ISOPROPYLIDENE 5 O (4 CHLOROBENZOYL) ALPHA DEXTRO ALLOFURANOSE; MAGNESIUM; NUCLEOSIDE DERIVATIVE; PHOSPHATE; REAGENT; UNCLASSIFIED DRUG; XYLOSE;

ARTICLE; CRYSTAL STRUCTURE; CRYSTALLIZATION; PRIORITY JOURNAL; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 2342515283     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.03.082     Document Type: Article

References (57)

1. Blackburn G., England D.A., Kolkmann F. J. Chem. Soc., Chem. Commun. 1981;930-932
2. Blackburn G., Kent D.E., Kolkmann F. J. Chem. Soc., Chem. Commun. 1981;1188-1190
3. McKenna C.E., Shen P.-D. J. Org. Chem. 46:1981;4573-4576
4. Chambers R.D., Jaouhari R., O'Hagan D. Tetrahedron. 45:1989;5101-5108
5. Chambers R.D., O'Hagan D., Lamont R.B., Jain S.C. J. Chem. Soc., Chem. Commun. 1990;1053-1054
6. Nieschalk J., Batsanov A.S., O'Hagan D., Howard J.A.K. Tetrahedron. 52:1996;165-176
7. Tatcher G.R., Campbell A.S. J. Org. Chem. 58:1993;2272-2281
8. Berkowitz D.B., Bose M. J. Fluorine Chem. 112:2001;13-33
9. Blackburn G.M., Kent D.E., Kolkmann F. J. Chem. Soc., Perkin Trans. 1. 1984;1119-1125
10. Blackburn G.M., Guo M.-J., Langston S.P., Taylor G.E. Tetrahedron Lett. 31:1990;5637-5640
11. Blackburn G.M., Langston S.P. Tetrahedron Lett. 32:1991;6425-6428
12. Matulic-Adamic J., Usman N. Tetrahedron Lett. 35:1994;3227-3230
13. Matulic-Adamic J., Haeberli P., Usman N. J. Org. Chem. 60:1995;2563-2569
14. Levy S.G., Wasson B., Carson D.A., Cottam H.B. Synthesis. 1996;843-846
15. Obayashi M., Ito E., Kondo K. Tetrahedron Lett. 23:1982;2323-2326
16. Burton D.J., Yang Z.-Y. Tetrahedron. 48:1992;189-275
17. Piettre S.R. Tetrahedron Lett. 37:1996;2233-2236
18. Herpin T.F., Houlton J.S., Motherwell W.B., Roberts B.P., Weibel J.-M. J. Chem. Soc., Chem. Commun. 1996;613-614
19. Herpin T.F., Motherwell W.B., Roberts B.P., Roland S., Weibel J.-M. Tetrahedron. 53:1997;15085-15100
20. Kovensky J., McNeil M., Sinaÿ P. J. Org. Chem. 64:1999;6202-6205
21. Lequeux T.P., Percy J.M. Synlett. 1995;361-362
22. Berkowitz D.B., Eggen M., Shen Q., Shoemaker R.K. J. Org. Chem. 61:1996;4666-4675
23. Blades K., Cockerill G.S., Easterfield H.J., Lequeux T.P., Percy J.M. Chem. Commun. 1996;1615-1616
24. Blades K., Lapôtre D., Percy J.M. Tetrahedron Lett. 38:1997;5895-5898
25. Blades K., Percy J.M. Tetrahedron Lett. 39:1998;9085-9088
26. Murano T., Muroyama S., Yokomatsu T., Shibuya S. Synlett. 2002;1657-1660
27. Murano T., Yuasa Y., Muroyama S., Yokomatsu T., Shibuya S. Tetrahedron. 59:2003;9059-9073
28. Murano T., Yuasa Y., Kobayakawa H., Yokomatsu T., Shibuya S. Tetrahedron. 59:2003;10223-10230
29. Blades K., Lequeux T.P., Percy J.M. Chem. Commun. 1996;1457-1458
30. Yokomatsu T., Katayama S., Shibuya S. Chem. Commun. 2001;1878-1879
31. Yokomatsu T., Suemune K., Murano T., Shibuya S. Heterocycles. 56:2002;273-282
32. Butt A.H., Kariuki B.M., Percy J.M., Spencer N.S. Chem. Commun. 2002;682-683
33. Yokomatsu T., Kato J., Sakuma C., Shibuya S. Synlett. 2003;1407-1410
34. Butt A.H., Percy J.M., Spencer N.S. Chem. Commun. 2000;1691-1692
35. Lopin C., Gautier A., Gouhier G., Piettre S.R. J. Am. Chem. Soc. 124:2002;14668-14678
36. Altona C., Sundaralingam M. J. Am. Chem. Soc. 94:1972;8205-8212
37. Altona C., Sundaralingam M. J. Am. Chem. Soc. 95:1973;2333-2334
38. Thibaudeau C., Plavec J., Garg N., Papchikhin A., Chattopadhyaya J. J. Am. Chem. Soc. 116:1994;4038-4043
39. Freier S.M., Altmann K.-H. Nucleic Acids Res. 25:1997;4429-4443
40. Bozo E., Boros S., Kuszmann J., Gacs-Baitz E., Parkanyi L. Carbohydr. Res. 308:1998;297-310
41. Marko I.E., Ates A., Gautier A., Leroy B., Plancher J.-M., Quesnel Y., Vanherck J.-C. Angew. Chem., Int. Ed. 38:1999;3207-3209
42. Benzoate 10 was prepared in 79% isolated yield according to literature procedure. See Nomura M., Sato T., Washinosu M., Tanaka M., Asao T., Shuto S., Matsuda A. Tetrahedron. 58:2002;1279-1288
43. De Lucca L., Giacomelli G., Porcheddu A. Org. Lett. 3:2001;3041-3043
44. The desired adduct was isolated in only 21% yield. See Ref. 10
45. For the use of the corresponding oxygenated reagent, see: Waschbüsch R., Samadi M., Savignac P. J. Organomet. Chem. 529:1997;267-278
46. Presumably, 2d acted as a base in a competitive manner
47. 2Na) gave lower yields or were unsuccessful
48. Niedballa U., Vorbrüggen H. Angew. Chem., Int. Ed. Engl. 9:1970;461-462
49. Niedballa U., Vorbrüggen H. J. Org. Chem. 39:1974;3654-3660
50. Niedballa U., Vorbrüggen H. J. Org. Chem. 39:1974;3660-3663
51. Niedballa U., Vorbrüggen H. J. Org. Chem. 39:1974;3664-3667
52. Niedballa U., Vorbrüggen H. J. Org. Chem. 39:1974;3668-3671
53. Niedballa U., Vorbrüggen H. J. Org. Chem. 39:1974;3672-3674
54. Niedballa U., Vorbrüggen H. J. Org. Chem. 41:1976;2084-2086
55. Vorbrüggen H., Bennua B. Tetrahedron Lett. 39:1978;1339-1342
56. Vorbrüggen H., Krolikiewicz K., Bennua B. Chem. Ber. 114:1981;1234-1255
57. Vorbrüggen H., Hölfe G. Chem. Ber. 114:1981;1256-1268