Synthesis of 1-phosphonoalkylidene and -arylidene derivatives of nucleosides

Tetrahedron Letters

Volumn 37, Issue 20, 1996, Pages 3497-3500

  Endová, Magdalena ^a   Masojídková, Milena ^a   Buděšínský, Miloš ^a   Rosenberg, Ivan ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0343446111     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00562-X     Document Type: Article

References (33)

1. a) Scheit K. H. Nucleotides with Modified Phosphate Groups. In Nucleotide Analogs. Synthesis and Biological Function; John Wiley and Sons, Inc.: New York, 1980; pp. 96-141;
2. b) Holy A. Isopolar Phosphorus-Modified Nucleotide Analogues. In Phosphorus Chemistry Directed Towards Biology; Stec S.J. Ed.; Pergamon Press: Oxford, 1980; pp. 53-64;
3. c) Holý A. Advances in Antiviral Drug Design 1993, 1, 179-231.
4. a) Albrecht H.P.; Jones H.G.; Moffat J.G. Tetrahedron 1984, 40, 79-85;
5. b) De Clercq E.; Holy A.; Rosenberg I.; Sakuma T.; Balzarini J.; Maudgal P.C. Nature 1986, 323, 464-467;
6. c)Tanaka H.; Fukui M.; Haraguchi K.; Masaki M.; Miysaka T. Tetrahedron Lett. 1989, 30, 2567-2570;
7. d) Jie L.; Van Aerschot A.; Balzarini J.; Janssen G.; Busson R.; Hoogmartens J.; De Clercq E.; Herdewijn P. J. Med. Chem. 1990, 33, 2481-2487;
8. e) Yoannidis P.; Classon B.; Samuelsson B.; Kvarnström I. Acta Chem. Scand. 1991, 45, 746-750;
9. f) Secrist J.A.; Riggs R.M.; Comber R.N.; Montgomery J.G. NucleosidesNucleotides 1992, 11, 947-956;
10. g) McEldoon W.L.; Wiemer D.F. Tetrahedron 1995, 51, 7131-7148.
11. a) Holý A.; Rosenberg I. Collect. Czech. Chem. Commun. 1982, 47, 3447-3463;
12. b) Rosenberg I.; Holý A. ibid. 1983, 48, 778-789;
13. c) Rosenberg I.; Holý A. ibid. 1985, 50, 1507-1513;
14. d) Rosenberg I.; Holý A. ibid 1987, 52, 2572-2588.
15. a) Veselý J.; Rosenberg I.; Holý A. Collect. Czech. Chem. Commun. 1982, 47, 3464-3469;
16. b) Horská K.; Rosenberg I.; Holý A.; Sebesta K. ibid. 1983, 48, 1352-1357;
17. c) Veselý J.; Rosenberg I.; Holý A. ibid. 1983, 48, 1783-1787;
18. d) Horská K.; Cvekl A.; Rosenberg I.; Holý A.; Šebesta K. ibid. 1990, 55, 2100-2109.
19. a) Masojídková M.; Zajíček J.; Buděšínský M.; Rosenberg I.; Holý A. Collect. Czech. Chem. Commun. 1985, 50, 1899-1906;
20. b) Zajiček J.; Rosenberg I.; Fazakerley G.V.; Guschlbauer W.; Holý A.; Točík Z.; Liboska R. ibid., submitted.
21. a) Costisella B.; Gross H. J. Prakt. Chem. 1977, 319, 8-16;
22. b) Mikolajczyk M.; Graczyk P.P. Tetrahedron 1992, 48, 4209-4230.
23. Dietsche W. Liebigs Ann. Chem. 1968, 712, 21-27.
24. a) Gaffney B.L.; Marky L.A.; Jones R.A. Tetrahedron 1984, 40, 3-13;
25. b) Chládek S.; Žemlička J.; Šorm F. Collect. Czech. Chem. Commun. 1966, 31, 1785-1802;
26. c) Fromageot H.P.M.; Griffin B.E.; Reese C.B.; Sulston J.E Tetrahedron 1967, 23, 2315-2331.
27. 8b,c and these compounds (1 mmol) were treated with chlorodiethylphosphite (2 mmol) in acetonitrile (10 ml) under argon atmosphere. Reaction temperature was varied according to the reactivity of the orthoester (see Table 1). The course of the reaction was followed by TLC (chloroform-ethanol mixture). After disappearance of the starting material the reaction was quenched by addition of the mixture of 1M TEAB-ethanol (1:1; 5 ml). The resulting mixture was concentrated in vacuo and the residue was purified by silica gel chromatography (chloroform-ethanol gradient mixture).
28. Bz ... N-6-benzoyladenin-9-yl.
29. Horwitz J.P.; Chua J.; Urbanski J. A.; Noel M. J. Org. Chem. 1963, 28, 942-944.
30. + form.
31. a) Bothner-By A.A.; Stephens R.L.; Jeanloz R.W. J. Am. Chem. Soc. 1984, 106, 811-813;
32. b) Bax A.; Davis D.G. J. Magn. Reson. 1985, 63, 207-213;
33. 6DMSO; temp. 20°C). Experimental parameters for isomeric pair of 5′-deprotected compounds 8 (mixing time 250 ms; spectral width 4314 Hz, acquisition time 0.119 s; relaxation delay 1.8 s; 16 transients accumulated for each of 359 increments; data matrix zero filled to 2K × 2K data points before FT).