Highly Effective Synthesis of
C-5-Substituted 2′-Deoxyuridine Using Suzuki-Miyaura
Cross-Coupling in Water

Guillaume Sartori; Gérald Enderlin; Gwénaelle Hervé; Christophe Len

doi:10.1055/s-0031-1289709

PAPER

Highly Effective Synthesis of C-5-Substituted 2′-Deoxyuridine Using Suzuki-Miyaura Cross-Coupling in Water

Guillaume Sartori, Gérald Enderlin, Gwénaelle Hervé, Christophe Len*
Transformations Intégrées de la Matière Renouvelable, UTC-ESCOM, Centre de recherche Royallieu, BP 20529, 60205 Compiègne, France
Fax: +33(3)44971591; e-Mail: christophe.len@utc.fr;

Abstract

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Abstract

An efficient protocol to provide a series of C-5-substituted 2′-deoxyuridine derivatives using a palladium-catalyzed Suzuki-Miyaura cross-coupling reaction in water has been established. Starting from 2′-deoxyuridine derivatives, the target nucleoside analogues were obtained in good yields with low levels of palladium loading without protection of any hydroxyl group of the glycone moiety.

Key words

cross-coupling - Suzuki-Miyaura - nucleosides - green chemistry

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References

<A NAME="RZ109411SS-1A">1a</A> Cihlar T. Ray AS. Antiviral Res. 2010, 85: 39

<A NAME="RZ109411SS-1B">1b</A> De Clercq E. Antiviral Res. 2010, 85: 19

<A NAME="RZ109411SS-1C">1c</A> De Clercq E. Curr. Opin. Pharmacol. 2010, 10: 507

<A NAME="RZ109411SS-2A">2a</A> Mitsuya H. Weinhold KJ. Furman PA. StClair MH. Lehrman SN. Gallo RC. Bolognesi D. Barry DW. Broder S. Proc. Natl. Acad. Sci. U.S.A. 1985, 82: 7096

<A NAME="RZ109411SS-2B">2b</A> Furman PA. Fyfe JA. StClair MH. Weinhold KJ. Rideout L. Freeman GA. Lehrman SN. Bolognesi DP. Broder S. Mitsuya H. Proc. Natl. Acad. Sci. U.S.A. 1986, 83: 8333

<A NAME="RZ109411SS-3A">3a</A> Andrei G. Snoeck R. Viruses 2010, 2: 2803

<A NAME="RZ109411SS-3B">3b</A> De Clercq E. Antonin H. Nat. Rev. Drug Discovery 2005, 4: 928

<A NAME="RZ109411SS-3C">3c</A> Holy A. Curr. Pharm. Des. 2003, 9: 2567

<A NAME="RZ109411SS-3D">3d</A> Gao H. Mitra AK. Synthesis 2000, 329

<A NAME="RZ109411SS-3E">3e</A> Chu CK. Cutler SJ. J. Heterocycl. Chem. 1986, 23: 289

<A NAME="RZ109411SS-4A">4a</A> Mathe C. Gosselin G. Antiviral Res. 2006, 71: 276

<A NAME="RZ109411SS-4B">4b</A> Gumina G. Chong Y. Choo H. Song GY. Chu CK. Curr. Top. Med. Chem. (Sharjah, United Arab Emirates) 2002, 2: 1065

<A NAME="RZ109411SS-4C">4c</A> Cheng YC. Antiviral Chem. Chemother. 2001, 12: 5

<A NAME="RZ109411SS-4D">4d</A> Gumina G. Song GY. Chu CK. FEMS Microbiol. Lett. 2001, 202: 9

<A NAME="RZ109411SS-4E">4e</A> Dutschman GE. Bridges EG. Liu SH. Gullen E. Guo X. Kukhanova M. Cheng YC. Antimicrob. Agents Chemother. 1998, 42: 1799

<A NAME="RZ109411SS-4F">4f</A> Wang P. Hong JH. Cooperwood JS. Chu CK. Antiviral Res. 1998, 40: 19

<A NAME="RZ109411SS-4G">4g</A> Schinazi RF. McMillan A. Cannon D. Mathis R. Lloyd RM. Peck A. Sommadossi JP. StClair MH. Wilson J. Furman PA. Painter G. Choi WB. Liotta DC. Antimicrob. Agents Chemother. 1992, 36: 2423

<A NAME="RZ109411SS-5A">5a</A> Yokoyama M. Synthesis 2000, 1637

<A NAME="RZ109411SS-5B">5b</A> Merino P. Tejero T. Delso I. Curr. Med. Chem. 2008, 15: 954

<A NAME="RZ109411SS-5C">5c</A> Merino P. Curr. Med. Chem. 2006, 13: 539

<A NAME="RZ109411SS-5D">5d</A> De Muys JM. Gourdeau H. Nguyen-Ba N. Taylor DL. Ahmed PS. Mansour T. Locas C. Richard N. Wainberg MA. Rando RF. Antimicrob. Agents Chemother. 1999, 43: 1835

<A NAME="RZ109411SS-6A">6a</A> Stambasky J. Hocek M. Kocovsky P. Chem. Rev. 2009, 109: 6729

<A NAME="RZ109411SS-6B">6b</A> Enderlin G. Taillefumier C. Didierjean C. Chapleur Y. J. Org. Chem. 2009, 74: 8388

<A NAME="RZ109411SS-6C">6c</A> Shaban MAE. Nasr AZ. Adv. Heterocycl. Chem. 1997, 68: 223

<A NAME="RZ109411SS-6D">6d</A> Shaban MAE. Adv. Heterocycl. Chem. 1997, 70: 163

<A NAME="RZ109411SS-6E">6e</A> Hacksell U. Daves GD. Prog. Med. Chem. 1985, 22: 1

<A NAME="RZ109411SS-6F">6f</A> Hanessian S. Pernet A. Adv. Carbohydr. Chem. Biochem. 1976, 33: 111

<A NAME="RZ109411SS-6G">6g</A> Daves GD. Cheng CC. Prog. Med. Chem. 1976, 13: 304

<A NAME="RZ109411SS-7A">7a</A> Lebreton J. Escudier JM. Arzel L. Len C. Chem. Rev. 2010, 110: 3371

<A NAME="RZ109411SS-7B">7b</A> Mathe C. Perigaud C. Eur. J. Org. Chem. 2008, 1489

<A NAME="RZ109411SS-7C">7c</A> Jørgensen AS. Shaikh KI. Enderlin G. Ivarsen E. Kumar S. Nielsen P. Org. Biomol. Chem. 2011, 9: 1381

<A NAME="RZ109411SS-7D">7d</A> Enderlin G. Nielsen P. J. Org. Chem. 2008, 73: 6891

<A NAME="RZ109411SS-8A">8a</A> Mieczkowski A. Roy V. Agrofoglio LA. Chem. Rev. 2010, 110: 1828

<A NAME="RZ109411SS-8B">8b</A> Mieczkowski A. Peltier P. Zevaco T. Agrofoglio LA. Tetrahedron 2009, 65: 4053

<A NAME="RZ109411SS-8C">8c</A> Len C. Mondon M. Lebreton J. Tetrahedron 2008, 64: 7453

<A NAME="RZ109411SS-8D">8d</A> Zhong S. Mondon M. Pilard S. Len C. Tetrahedron 2008, 64: 7828

<A NAME="RZ109411SS-9A">9a</A> Bilenko V. Spannenberg A. Baumann W. Komarov I. Börner A. Tetrahedron: Asymmetry 2006, 17: 2082

<A NAME="RZ109411SS-9B">9b</A> Maier M.-E. Reuter S. Synlett 1995, 1029

<A NAME="RZ109411SS-9C">9c</A> Behr S. Hegemann K. Schimanski H. Fröhlich R. Haufe G. Eur. J. Org. Chem. 2004, 3884

<A NAME="RZ109411SS-9D">9d</A> Gourdel Y. Pellon P. Toupet L. Le Corre M. Tetrahedron Lett. 1994, 35: 1197

<A NAME="RZ109411SS-9E">9e</A> Schmidt B. Staude L. Kelling A. Schilde U. Eur. J. Org. Chem. 2011, 1721

<A NAME="RZ109411SS-10A">10a</A> Wilhelmsson LM. Quarterly Rev. Biophys. 2010, 43: 159

<A NAME="RZ109411SS-10B">10b</A> Pesnot T. Wagner GK. Org. Biomol. Chem. 2008, 6: 2884

<A NAME="RZ109411SS-10C">10c</A> Wanninger-Weib C. Wagenknecht HA. Eur. J. Org. Chem. 2008, 64

<A NAME="RZ109411SS-10D">10d</A> Ehrenschwender T. Wagenknecht HA. Synthesis 2008, 3657

<A NAME="RZ109411SS-10E">10e</A> Srivatsan SG. Tor Y. J. Am. Chem. Soc. 2007, 129: 2044

<A NAME="RZ109411SS-10F">10f</A> Greco NJ. Tor Y. Tetrahedron 2007, 63: 3515

<A NAME="RZ109411SS-10G">10g</A> Mayer E. Valis L. Huber R. Amann N. Wagenknecht HA. Synthesis 2003, 2335

<A NAME="RZ109411SS-11A">11a</A> Stille JK. Angew. Chem., Int. Ed. Engl. 1986, 25: 508

<A NAME="RZ109411SS-11B">11b</A> Stille JK. Pure Appl. Chem. 1985, 57: 1771

<A NAME="RZ109411SS-11C">11c</A> Mitchell TN. Synthesis 1992, 803

<A NAME="RZ109411SS-11D">11d</A> Miyaura N. Yanagi T. Suzuki A. Synth. Commun. 1981, 11: 513

<A NAME="RZ109411SS-11E">11e</A> Miyaura N. Suzuki A. Chem. Rev. 1995, 95: 2457

<A NAME="RZ109411SS-11F">11f</A> Miyaura N. Cross-Coupling Reactions: A Practical Guide Springer; New York: 2002.

<A NAME="RZ109411SS-12A">12a</A> Hapiot F. Ponchel A. Tilloy S. Monflier E. C. R. Chim. 2011, 14: 149

<A NAME="RZ109411SS-12B">12b</A> Fihri A. Luart D. Len C. Solhi A. Chevrin C. Polshettiwar V. Dalton Trans. 2011, 3116

<A NAME="RZ109411SS-12C">12c</A> Polshettiwar V. Decottignies A. Len C. Fihri A. ChemSusChem 2010, 5: 502

<A NAME="RZ109411SS-13A">13a</A> Agrofoglio LA. Gillaizeau I. Saito Y. Chem. Rev. 2003, 103: 1875

<A NAME="RZ109411SS-13B">13b</A> Lakshman MK. J. Organomet. Chem. 2002, 653: 234

<A NAME="RZ109411SS-13C">13c</A> Abeijon P. Blanco JM. Caamano O. Fernandez F. Garcia MD. Garcia-Mera X. Rodriguez-Borges JE. Balzarini J. De Clercq E. Synthesis 2009, 2766

<A NAME="RZ109411SS-14A">14a</A> Onuma S. Kumamoto H. Kawato M. Tanaka H. Tetrahedron 2002, 58: 2497

<A NAME="RZ109411SS-14B">14b</A> Haraguchi K. Itoh Y. Tanaka H. Akita M. Miyasaka T. Tetrahedron 1993, 49: 1371

<A NAME="RZ109411SS-14C">14c</A> Len C. Mackenzie G. Tetrahedron 2006, 62: 9085

<A NAME="RZ109411SS-15A">15a</A> Ewing DF. Fahmi N. Len C. Mackenzie G. Ronco G. Villa P. Shaw G. Nucleosides Nucleotides 1999, 18: 2613

<A NAME="RZ109411SS-15B">15b</A> Ewing DF. Fahmi N. Len C. Mackenzie G. Pranzo A. J. Chem. Soc., Perkin Trans. 1 2000, 3561

<A NAME="RZ109411SS-15C">15c</A> Lipka-Belloli E. Len C. Mackenzie G. Ronco G. Bonte JP. Vaccher C. J. Chromatogr., A 2001, 943: 91

<A NAME="RZ109411SS-15D">15d</A> Ewing DF. Len C. Mackenzie G. Ronco G. Villa P. Tetrahedron: Asymmetry 2000, 11: 4995

<A NAME="RZ109411SS-15E">15e</A> Selouane A. Vaccher C. Villa P. Postel D. Len C. Tetrahedron: Asymmetry 2002, 13: 407

<A NAME="RZ109411SS-15F">15f</A> Pilard S. Riboul D. Glaçon V. Moitessier N. Chapleur Y. Postel D. Len C. Tetrahedron: Asymmetry 2002, 13: 529

<A NAME="RZ109411SS-15G">15g</A> Egron D. Perigaud C. Aubertin AM. Faraj A. Selouane A. Postel D. Len C. Bioorg. Med. Chem. Lett. 2003, 13: 4473

<A NAME="RZ109411SS-16A">16a</A> Western EC. Daft JR. Johnson EM. Gannett PM. Shaughnessy KH. J. Org. Chem. 2003, 68: 6767

<A NAME="RZ109411SS-16B">16b</A> Okamoto A. Inasaki T. Saito I. Tetrahedron Lett. 2005, 46: 791

<A NAME="RZ109411SS-16C">16c</A> Mizuta M. Banba JI. Kanamori T. Ohkubo A. Sekine M. Seio K. Nucleic Acids Symp. Ser. 2007, 51: 25

<A NAME="RZ109411SS-16D">16d</A> Kalachova L. Pohl R. Hocek M. Synthesis 2009, 105

<A NAME="RZ109411SS-16E">16e</A> Kogler M. Vanderhoydonck B. De Jonghe S. Rozenski J. Van Belle K. Herman J. Louat T. Parchina A. Sibley C. Lescrinier E. Herdewijn P. J. Med. Chem. 2011, 54: 4847

<A NAME="RZ109411SS-16F">16f</A> Hasnik Z. Pohl R. Hocek M. Synthesis 2009, 1309

<A NAME="RZ109411SS-17">17</A> Qu GR. Xin PY. Niu HY. Jin X. Guo XT. Yang XN. Guo HM. Tetrahedron 2011, 67: 9099

<A NAME="RZ109411SS-18">18</A> Shaughnessy KH. Chem. Rev. 2009, 109: 643

<A NAME="RZ109411SS-19">19</A> Chand G. Mertes MP. J. Org. Chem. 1987, 52: 3625

<A NAME="RZ109411SS-20">20</A> Aucagne V. Berteina-Raboin S. Guenot P. Agrofoglio LA. J. Comb. Chem. 2004, 6: 717