Biopolym. Cell. 1998; 14(3):246-251.
Methods
Study of iodination mechanism of 5'-O-prolecled pyrimidine Hucleosides in Arbuzov reaction conditions
1Kostina V. G., 1Shalamay A. S., 1Usenko L. S., 1Gladkaya V. A.
  1. Institute of Molecular Biology and Genetics, NAS of Ukraine
    150, Akademika Zabolotnoho Str., Kyiv, Ukraine, 03680

Abstract

Tlw mechaflism of iodination of C2- and C3-atoms of ribofuranose In pyrimidine nudeosides in conditions of Arbuzov reaction have been studied. Intermediate 2'- and 3''-quaziphosphonium salts where, shown, to be involved in further intramolecular nudeophilic reactions, the resulting 2',3'-diiododerivative being deiodinated and transformed into correspondent 2',3'-didehydro-2'-3'-dideoxynuc-leosides.

References

[1] Krayevsky AA, Watanabe KA. Modified nucleosides as anti-AIDS drugs: Current status and perspectives. Moscow, 1993. C. 212 p.
[2] Baba M, Pauwels R, Herdewijn P, De Clercq E, Desmyter J, Vandeputte M. Both 2',3'-dideoxythymidine and its 2',3'-unsaturated derivative (2',3'-dideoxythymidinene) are potent and selective inhibitors of human immunodeficiency virus replication in vitro. Biochem Biophys Res Commun. 1987;142(1):128-34.
[3] Bristal-Meyers Sguibb Company. Original monography. Drugs of the Future. 1996; 21(10): 1080-92.
[4] Samukov VV, Ofitserov VI. Synthesis of 2',3'-dideoxynucleosides. Bioorg Khim. 1983; 9 (1):52-9
[5] Van Aerschot A, Everaert D, Balzarini J, Augustyns K, Jie L, Janssen G, Peeters O, Blaton N, De Ranter C, De Clercq E, et al. Synthesis and anti-HIV evaluation of 2',3'-dideoxyribo-5-chloropyrimidine analogues: reduced toxicity of 5-chlorinated 2',3'-dideoxynucleosides. J Med Chem. 1990;33(6):1833-9.
[6] Verheyden JPH, Moffatt JG. Halosugar nucleosides. II. Iodination of secondary hydroxyl groups of nucleosides with methyltriphenoxyphosphonium iodide. J Org Chem. 1970;35(9):2868–77.
[7] Verheyden JP, Moffatt JG. Halo sugar nucleosides. 3. Reactions for the chlorination and bromination of nucleoside hydroxyl groups. J Org Chem. 1972;37(14):2289-99.
[8] Codington JF, Doerr IL, Fox JJ. Nucleosides. XVIII. Synthesis of 2'-Fluorothymidine, 2'-Fluorodeoxyuridine, and Other 2'-Halogeno-2'-Deoxy Nucleosides 1,2. J Org Chem. 1969; 29(3): 558-564.
[9] Garegg PJ, Samuelsson B. One-step conversion of vicinal diols into olefins, using a novel reagent system. Synthesis. 1979;1979(06):469–70.
[10] Garegg PJ, Samuelsson B. Conversion of vicinal diols into olefins using triphenylphosphine and triiodoimidazole. synthesis. 1979;1979(10):813–4.
[11] Garegg PJ, Samuelsson B. Novel reagent system for converting a hydroxy-group into an iodo-group in carbohydrates with inversion of configuration. Part 2. Journal of the Chemical Society, Perkin Transactions 1. 1980;2866-8.
[12] Kostina VG, Shalamay AS, Vsenko LS. Synthesis of 2', 3'-didehydro-2', 3'-dideoxyuridine with following addition of triphenylphosphonium iodides. Biopolym Cell. 1996; 12(4):100-4.
[13] Kostina VG, Shalamay AS, Usenko LS, Gladkaya VA. Recyclizalion of O2,2'-cyclopyrimidinnucleosicies with the use of haloid derivatives of threevalent phosphor and quasiphosphonic sails. Biopolym Cell. 1997; 13(3):197-201.
[14] Fromageot HPM, Griffin BE, Reese CB, Sulston JE. The synthesis of oligoribonucleotides—III. Tetrahedron. 1967;23(5):2315–31.