3′ - Thiouridylyl - (3′ → 5′) - uridine

Tetrahedron Letters

Volumn 37, Issue 6, 1996, Pages 925-928

  Liu, Xiaohai ^a   Reese, Colin B ^a  

^a KING'S COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

URIDINE DERIVATIVE;

ARTICLE; DRUG STABILITY;

EID: 0030032337     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02281-3     Document Type: Article

References (21)

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3. Reese, C. B. in Nucleic Acids and Molecular Biology, Vol. 3, Eckstein, F. and Lilley, D. M. J., Eds., Springer, Berlin, 1989, pp. 164-181.
4. Reese, C. B.; Simons, C.; Zhang, P.-Z. J. Chem Soc., Chem. Commun. 1994, 1809-1810.
5. Liu, X.; Reese, C. B. Tetrahedron Lett. 1995, 36, 3413-3416.
6. This work was first presented in outline on 7th August 1995 at a Nucleic Acids Symposium held at Noordwijkerhout in the Netherlands.
7. Johnson, R.; Joshi, B. V.; Reese, C. B. J. Chem. Soc., Chem. Commun., 1994, 133-134.
8. Mitsunobu, O. Synthesis, 1981, 1-28.
9. 10.
10. Yung, N. C. ; Fox, J. J. J. Am. Chem. Soc., 1961, 83, 3060-3066.
11. 7 for 2-nitrophenylsulfanyl chloride.
12. Reese, C. B.; Thompson E. A. J. Chem. Soc., Perkin Trans. 1, 1988, 2881-2885.
13. P,H 602.8).
14. Lohrmann, R.; Khorana, H. G. J. Am. Chem. Soc., 1964, 86, 4188-4194.
15. Li, X.; Scott, G. K.; Baxter, A. D.; Taylor, R. J.; Vyle, J. S.; Cosstick, R. J. Chem. Soc., Perkin Trans. 1, 1994, 2123-2129.
16. 260 units.
17. 2O] 37.1.
18. Müller, C. E.; Roth, H. J. Tetrahedron Lett., 1990, 31, 501-502.
19. -3 aqueous triethylammonium acetate (pH 7.0) (3:97 to 20:80 v/v) over 10 min, followed by a linear gradient (20:80 to 30:70 v/v) over a further 5 min]. Retention times for uridine 9, 3′-thiouridine 2′,3′-cyclic phosphorothioate 13, 3′-thiouridine 3′-phosphorothioate 14 and 3′-thiouridylyl-(3′→5′)-uridine 3 were 3.37, 4.83, 6.27 and 7.76 min, respectively.
20. The formation of 3′-thiouridine 3′-phosphorothioate 14 was presumably due to the presence of traces of moisture in the acetic acid.
21. -3 aqueous triethylammonium acetate (pH 7.0) (3:97 to 7:93 v/v) over 10 min]. The numbers in parentheses represent percentages of the total absorbance at 260 nm.