Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Comparative Study on the Effectiveness of Azidation Reaction for the Synthesis of Xylo-azidonucleoside Analogues by Mitsunobu and Lithium Azide Methods

Author(s): Sheneya Festus*, Sudheesh Devadas, Akshaya Kudiliparambil Subramanian and Krishnakumar S. Kollappillil

Volume 19, Issue 12, 2022

Published on: 05 August, 2022

Page: [1141 - 1144] Pages: 4

DOI: 10.2174/1570178619666220621112018

Price: $65

Abstract

Many therapeutically important nucleoside analogues can be synthesized from versatile azidonucleoside intermediates. We have synthesized 3’-xylo-azidonucleoside analogues of thymidine and 2’-deoxyadenosine via Mitsunobu-DPPA and triflate-lithium azide strategies. On comparing the two azidation strategies on nucleoside analogues, we found that Mitsunobu-DPPA azidation is better than triflate-lithium azide azidation in terms of yield and reaction conditions.

Keywords: Mitsunobu, lithium azide, DPPA, triflate, nucleosides, azidation.

« Previous Next »
Graphical Abstract

[1]
Chu, C.K. Antiviral nucleosides: chiral synthesis and chemotherapy, 1st ed; Elsevier: The Netherlands, 2003.
[2]
el Kouni, M.H. Curr. Pharm. Des., 2002, 8(8), 581-593.
[http://dx.doi.org/10.2174/1381612024607171] [PMID: 11945160]
[3]
Mitsuya, H.; Weinhold, K.J.; Furman, P.A.; St Clair, M.H.; Lehrman, S.N.; Gallo, R.C.; Bolognesi, D.; Barry, D.W.; Broder, S. Proc. Natl. Acad. Sci. USA, 1985, 82(20), 7096-7100.
[http://dx.doi.org/10.1073/pnas.82.20.7096] [PMID: 2413459]
[4]
Han, J.; Funk, C.; Eyberg, J.; Bailer, S.; Richert, C. Chem. Biodivers., 2021, 18(1), e2000937.
[http://dx.doi.org/10.1002/cbdv.202000937] [PMID: 33270983]
[5]
Pathak, T. Chem. Rev., 2002, 102(5), 1623-1668.
[http://dx.doi.org/10.1021/cr0104532] [PMID: 11996546]
[6]
Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem. Int. Ed., 2005, 44(33), 5188-5240.
[http://dx.doi.org/10.1002/anie.200400657]
[7]
Honcharenko, M.; Honcharenko, D.; Strömberg, R. Bioconjug. Chem., 2019, 30(6), 1622-1628.
[http://dx.doi.org/10.1021/acs.bioconjchem.9b00217] [PMID: 31067031]
[8]
Wenska, M.; Alvira, M.; Steunenberg, P.; Stenberg, A.; Murtola, M.; Strömberg, R. Nucleic Acids Res., 2011, 39(20), 9047-9059.
[http://dx.doi.org/10.1093/nar/gkr603] [PMID: 21795380]
[9]
Zhang, R.; Liu, S.; Edgar, K.J. Carbohydr. Polym., 2017, 171, 1-8.
[http://dx.doi.org/10.1016/j.carbpol.2017.04.093] [PMID: 28578943]
[10]
Chapuis, H.; Strazewski, P. Tetrahedron, 2006, 62(51), 12108-12115.
[http://dx.doi.org/10.1016/j.tet.2006.09.045]
[11]
Charafeddine, A.; Dayoub, W.; Chapuis, H.; Strazewski, P. Chemistry, 2007, 13(19), 5566-5584.
[http://dx.doi.org/10.1002/chem.200700058] [PMID: 17455187]
[12]
Michel, B.Y.; Krishnakumar, K.S.; Strazewski, P. Synlett, 2008, 2008(16), 2461-2464.
[http://dx.doi.org/10.1055/s-2008-1078025]
[13]
Feng, L.S.; Zheng, M.J.; Zhao, F.; Liu, D. Arch. Pharm. (Weinheim), 2021, 354(1), e2000163.
[http://dx.doi.org/10.1002/ardp.202000163] [PMID: 32960467]
[14]
Besset, C.; Chambert, S.; Fenet, B.; Queneau, Y. Tetrahedron Lett., 2009, 50(50), 7043-7047.
[http://dx.doi.org/10.1016/j.tetlet.2009.09.173]
[15]
Liang, H. Synlett, 2008, 2008(16), 2554-2555.
[http://dx.doi.org/10.1055/s-2008-1067132]
[16]
Mukaiyama, T.; Kuroda, K.; Maruyama, Y.; Hayashi, Y. Chem. Lett., 2008, 37(10), 1072-1073.
[http://dx.doi.org/10.1246/cl.2008.1072]
[17]
Sagandira, C.R.; Watts, P. Synlett, 2020, 31(19), 1925-1929.
[http://dx.doi.org/10.1055/s-0039-1690878]
[18]
Błaszczyk, R. Synlett, 2008, 2008(02), 299-300.
[http://dx.doi.org/10.1055/s-2007-1000842]
[19]
Sivaguru, P.; Ning, Y.; Bi, X. Chem. Rev., 2021, 121(7), 4253-4307.
[http://dx.doi.org/10.1021/acs.chemrev.0c01124] [PMID: 33635623]
[20]
Almond, M.R.; Lowen, G.T.; Martin, G.E.; Rideout, J.L. Nucleosides Nucleotides, 1993, 12(9), 905-913.
[http://dx.doi.org/10.1080/07328319308018561]
[21]
Yamamoto, I.; Sekine, M.; Hata, T. J. Chem. Soc., Perkin Trans. 1, 1980, 1(0), 306-310.
[http://dx.doi.org/10.1039/P19800000306]
[22]
Horwitz, J.P.; Chua, J.; Noel, M. J. Org. Chem., 1964, 29(7), 2076-2078.
[http://dx.doi.org/10.1021/jo01030a546]
[23]
Sun, J.; Liu, X.; Li, H.; Duan, R.; Wu, J. Helv. Chim. Acta, 2012, 95(5), 772-779.
[http://dx.doi.org/10.1002/hlca.201100366]
[24]
Nguyen-Trung, N.Q.; Botta, O.; Terenzi, S.; Strazewski, P. J. Org. Chem., 2003, 68(5), 2038-2041.
[http://dx.doi.org/10.1021/jo026627c] [PMID: 12608833]
[25]
Lal, B.; Pramanik, B.N.; Manhas, M.S.; Bose, A.K. Tetrahedron Lett., 1977, 18(23), 1977-1980.
[http://dx.doi.org/10.1016/S0040-4039(01)83657-1]
[26]
Krishnakumar, K.S.; Strazewski, P. Synlett, 2010, 2010(07), 1055-1058.
[http://dx.doi.org/10.1055/s-0029-1219436]

Rights & Permissions Print Cite
Article Metrics
8
© 2025 Bentham Science Publishers | Privacy Policy