Phosphorylation of nucleoside derivatives with aryl phosphoramidochloridates
J.H. van Boom; P.M.J.B.rgers; R.C.ea; W.C.M.M.L.yten; A.B.J.V.nk; C.B.R.ese
Tetrahedron 31(23): 2953-2959
1975
ISSN/ISBN: 0040-4020
DOI: 10.1016/0040-4020(75)80318-8
Accession: 027142945
The preparation of three aryl phosphorocyclohexylamidochloridates (7a, 7b and 7c) and an aryl phosphoromorpholidochloridate (8) is described. These aryl phosphoramidochloridates react with 2′,3′-O-methoxymethylene-uridine, -4-N-anisoylcytidine and -6-N-anisoyladenosine (9a, 9b and 9c, respectively), in the presence of the 1-ethylimidazole derivative (11a) to give high yields of the corresponding fully-protected 5′-phosphoramidates (10).
PDF emailed within 0-6 h: $19.90
Related References
Szymańska, A.; Szymczak, M.; Boryski, J.; Stawiński, J.; Kraszewski, A.; Collu, G.; Sanna, G.; Giliberti, G.; Loddo, R.; La Colla, P. 2006: Aryl nucleoside H-phosphonates. Part 15: Synthesis, properties and, anti-HIV activity of aryl nucleoside 5'-alpha-hydroxyphosphonates Bioorganic and Medicinal Chemistry 14(6): 1924-1934Romanowska, J.; Szymańska-Michalak, A.; Boryski, J.; Stawiński, J.; Kraszewski, A.; Loddo, R.; Sanna, G.; Collu, G.; Secci, B.; La Colla, P. 2009: Aryl nucleoside H-phosphonates. Part 16: synthesis and anti-HIV-1 activity of di-aryl nucleoside phosphotriesters Bioorganic and Medicinal Chemistry 17(9): 3489-3498
Motomura, K.; Hirota, R.; Okada, M.; Ikeda, T.; Ishida, T.; Kuroda, A. 2014: A new subfamily of polyphosphate kinase 2 (class III PPK2) catalyzes both nucleoside monophosphate phosphorylation and nucleoside diphosphate phosphorylation Applied and environmental microbiology 80(8): 2602-2608
Cieslak, J.; Jankowska, J.; Szymczak, M.; Kers, A.; Kers, I.; Stawinski, J.; Kraszewski, A. 1999: Aryl nucleoside H-phosphonates - novel derivatives of controlled reactivity Nucleosides and Nucleotides 18(4-5): 937-938
Hunter, R.; Younis, Y.; Muhanji, C.I.; Curtin, T.-L.; Naidoo, K.J.; Petersen, M.; Bailey, C.M.; Basavapathruni, A.; Anderson, K.S. 2008: C-2-aryl O-substituted HI-236 derivatives as non-nucleoside HIV-1 reverse-transcriptase inhibitors Bioorganic and Medicinal Chemistry 16(24): 10270-10280
Babu, Y.S.; Elliott, A.J.; Montgomery, J.A.; MorrisPhilip, E.Jr.; Petty, S.L.; Walsh, D.A.; Williams, C.H. 1997: 9-Aryl- and 9-cycloalkylheteroatom-substituted derivatives of 9-deazaguanine, inhibitors of purine nucleoside phosphorylase Abstracts of Papers American Chemical Society 213(1-3): MEDI 295
Guo, R.-H.; Zhang, Q.; Ma, Y.-B.; Huang, X.-Y.; Luo, J.; Wang, L.-J.; Geng, C.-A.; Zhang, X.-M.; Zhou, J.; Jiang, Z.-Y.; Chen, J.-J. 2011: Synthesis and biological assay of 4-aryl-6-chloro-quinoline derivatives as novel non-nucleoside anti-HBV agents Bioorganic and Medicinal Chemistry 19(4): 1400-1408
Shimidzu, T.; Yamana, K.; Maikuma, S.; Oikawa, Y. 1983: Phosphine derivatives for selective phosphorylation of nucleoside and their application to oligonucleotide chemistry Nucleic Acids Symposium Series 12: 55-58
Rawal, R.K.; Katti, S.B.; Kaushik-Basu, N.; Arora, P.; Pan, Z. 2008: Non-nucleoside inhibitors of the hepatitis C virus NS5B RNA-dependant RNA polymerase: 2-aryl-3-heteroaryl-1,3-thiazolidin-4-one derivatives Bioorganic and Medicinal Chemistry Letters 18(23): 6110-6114
Xia, Y.; Qu, F.; Peng, L. 2010: Triazole nucleoside derivatives bearing aryl functionalities on the nucleobases show antiviral and anticancer activity Mini Reviews in Medicinal Chemistry 10(9): 806-821
Beer, D.; Meuwly, R.; Vasella, A. 1982: L erythro uronic acid derivatives as building blocks for nucleoside analogs synthesis of 4' c aryl d ribo nucleosides Helvetica Chimica Acta 65(8): 2570-2582
Carangio, A.; McGuigan, C.; Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J. 2001: Bicyclic nucleoside inhibitors of varicella-zoster virus (VZV): Pd-catalysed synthesis of 5-aryl derivatives and their biological evaluation Antiviral Chemistry and ChemoTherapy 12(3): 187-197
Kellner, H.A.; Schneiderwind, R.G.K.; Eckert, H.; Ugi, I.K. 1981: Bis(2,2,2-trichloro-1,1-dimethylethyl) Monochlorophosphate, a Selective Reagent for the Phosphorylation and Protection of the 5′-OH Group of Nucleoside Derivatives Angewandte Chemie International Edition in English 20(67): 577-578
Grachev, M.A.; Lukhtanov, E.A.; Mustaev, A.A. 1986: Synthesis of derivatives of nucleoside 5' monophosphates nucleoside 5' diphosphate and nucleoside 5' triphosphate with reactive groups attached to phosphate residues Bioorganicheskaya Khimiya 12(8): 1079-1087
Miles, D.W.; Inskeep, W.H.; Robins, M.J.; Winkley, M.W.; Robins, R.K.; Eyring, H. 2009: Circular dichroism of nucleoside derivatives. VII. the electronic structure and spectra of some simple nucleoside derivatives International Journal of Quantum Chemistry 3(S 3A): 129-145
Miles, D.W.; Robins, M.J.; Robins, R.K.; Eyring, H. 1969: Circular dichroism of nucleoside derivatives. VI. the optically active bands of adenine nucleoside derivatives Proceedings of the National Academy of Sciences of the United States of America 62(1): 22-29
Mitsugi, Koji; Kamimura, Akira; Okumura, Shingi; Katsuya, N. 1964: Bacterial synthesis of nucleotides. VII. Acceptor specificity of nucleoside phosphotransferase Phosphorylation of unusual ribo-nucleosides and their ribosyl derivatives Agr Biol Chem 28(12): 849-858
Koch, K.; Chen, Y.; Feng, J.Y.; Borroto-Esoda, K.; Deville-Bonne, D.; Gallois-Montbrun, S.; Janin, Jël.; Moréra, S. 2009: Nucleoside diphosphate kinase and the activation of antiviral phosphonate analogs of nucleotides: binding mode and phosphorylation of tenofovir derivatives Nucleosides Nucleotides and Nucleic Acids 28(8): 776-792
De Martino, G.; La Regina, G.; Ragno, R.; Coluccia, A.; Bergamini, A.; Ciaprini, C.; Sinistro, A.; Maga, G.; Crespan, E.; Artico, M.; Silvestri, R. 2006: Indolyl aryl sulphones as HIV-1 non-nucleoside reverse transcriptase inhibitors: synthesis, biological evaluation and binding mode studies of new derivatives at indole-2-carboxamide Antiviral Chemistry and ChemoTherapy 17(2): 59-77
Brill, W.K D.; Caruthers, M.H. 1988: Synthesis and p diastereomeric resolution of nucleoside 3' os alkyl and nucleoside 3' os aryl methylphosphonothioates Tetrahedron Letters 29(11): 1227-1230