Advanced search
Publication Cover
Organic Preparations and Procedures International
The New Journal for Organic Synthesis
Volume 50, 2018 - Issue 4
Submit an article Journal homepage
48
Views
4
CrossRef citations to date
0
Altmetric
Original Articles

An Operationally Simple One-Step Chemo- and Diastereoselective Synthesis of cis-5-Hydroxy-2-phosphono-2,5-dihydrofurans

Marwa HermiLaboratory of Heteroatom Organic Chemistry, Faculty of Sciences of Bizerte, University of Carthage, 7021-Jarzouna, Tunisia
,
Werner KaminskyDepartment of Chemistry, University of Washington, BOX 351700, Seattle, WA98195, USA
,
Cherif Ben NasrLaboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, Université de Carthage, 7021-Jarzouna, Tunisie
&
Soufiane TouilLaboratory of Heteroatom Organic Chemistry, Faculty of Sciences of Bizerte, University of Carthage, 7021-Jarzouna, TunisiaCorrespondence[email protected]
Pages 432-440 | Received 13 Oct 2017, Accepted 23 Feb 2018, Published online: 19 Oct 2018

References

  • T. G. Kilroy, T. P. O’Sullivan and P. J. Guiry, Eur. J. Org. Chem., 23, 4929 (2005).
  • H. Heaney and J. S. Ahn, “Comprehensive Heterocyclic Chemistry II”, Vol. 2, p. 297, A. R. Katritzky, C. W. Rees and E. F. V. Scriven, Eds.; Pergamon Press: Oxford, UK, 1996.
  • T. Eicher, S. Hauptmann and S. Andreas, “The Chemistry of Heterocycles: Structure, Reactions, Syntheses, and Applications”; Wiley-VCH: Weinheim, Germany, 2003, p. 52.
  • B. H. Lipshutz, Chem. Rev., 86, 795 (1986).
  • C. K. Chu, “Antiviral Nucleosides. Chiral Synthesis and Chemotherapy”, Amsterdam: Elsevier Science, 2003, p. 268.
  • P. Mohan and M. Baba, “Anti-AIDS Drug Development: Challenges Strategies and Prospects”, Chur: Harwood Academic Publishers, 1995, p. 40.
  • H. Mitsuya and S. Broder, Natl. Acad. Sci., 83, 1911 (1986).
  • D. M. Huryn, B. C. Sluboski, S. Y. Tam, L. J. Todaro, and M. Weigele, Tetraheron Lett., 30, 6259 (1989).
  • C. U. Kim, B. Y. Luh and J. C. Martin, J. Org. Chem., 56, 2642 (1991).
  • N. B. Dyatkina, E. A. Shirokova, F. Theil, S. M. Roberts and A. A. Krayevsky, Bioorg. Med. Chem. Lett., 6, 2639 (1996).
  • T. Wu, M. Froeyen, V. Kempeneers, C. Pannecouque, J. Wang, R. Busson, E. De Clercq and P. Herdewijn, J. Am. Chem. Soc., 127, 5056 (2005).
  • T. Cihlar, A. S. Ray, C. G. Boojamra, L. Zhang, H. Hui, G. Laflamme, J. E. Vela, D. Grant, J. Chen and F. Myrick, Antimicrob. Agents Chemother., 52, 655 (2008).
  • F. Liua, Y. Liua, R. G. Xua, G. Daia, L. X. Zhaod, Y. Wanga, H. M. Liua, F. W. Liu, C. Pannecouquee and P. Herdewijn, Chem. Biodivers., 12, 813 (2015).
  • C. Liu, S. G. Dumbre, C. Pannecouque, C. Huang, R. G. Ptak, M. G. Murray, S. De Jonghe, and P. Herdewijn, J. Med. Chem., 59, 9513 (2016).
  • E. De Clercq, Biochem. Pharmacol., 82, 99 (2011).
  • E. De Clercq, R. L. Mackman and T. Cihlar, “Antiviral Drug Strategies”, first edition. edited by Erik De Clercq. 2011 Wiley-VCH Verlag GmbH & Co. KGaA, pp. 91–128.
  • F. Pertusati, M. Serpi and C. McGuigan, Antivir. Chem. Chemother., 22, 181 (2012).
  • U. Pradere, E. C. Garnier-Amblard, S. J. Coats, F. Amblard and R. F. Schinazi, Chem. Rev., 114, 9154 (2014).
  • V. Ch. Christov, I. E. Ismailov and I. K. Ivanov, Molecules, 20, 7263 (2015).
  • V. Ch. Christov, H. H. Hasanov and I. K. Ivanov, Global J. Pure Appl. Chem. Res., 3, 20 (2015).
  • A. V. Borodachev and V. K. Brel, Russ. J. Gen. Chem., 85, 2754 (2015).
  • V. K. Brel and E. V. Abramkin, Mendeleev Commun., 12, 64 (2002).
  • I. Essid and S. Touil, Arkivoc, 98 (2013).
  • E. Chebil, M. Chamakhi and S. Touil, J. Sulfur Chem., 32, 249 (2011).
  • S. Touil and H. Zantour, Phosphorus, Sulfur Silicon Relat. Elem., 178, 353 (2003).
  • N. Said, S. Touil and H. Zantour, Phosphorus, Sulfur Silicon Rel. Elem., 179, 2487 (2004).
  • S. H. Demirdji, M. J. Haddadin and C. H. Issidorides, J. Heterocyclic Chem., 22, 495 (1985).
  • N. Kreutzkamp and W. Mengel, Arch. Pharm. (Weinheim), 300, 389 (1967).
  • C. E. Griffin and J. T. Brown, J. Org. Chem., 26, 853 (1961).
  • F. Ramirez, O. P. Madan and C. P. Smith, J. Org. Chem., 30, 2284 (1965).
  • L. M. Pevzner, V. M. Ignat’ev and B. I. Z. Ionin, Obshch. Kim, 64, 135 (1994) (Chem. Abstr., 121, 134268u (1994)).
  • Y. M. Dangyan, M. R. Tirakyan, G. A. Panosyan, V. I. Denisenko and S. O. Badanyan, Zh. Obshch. Kim., 58, 1240 (1988) (Chem. Abstr., 110, 135363f (1989)).
  • S. Touil and H. Zantour, Phosphorus, Sulfur Silicon Relat. Elem., 131, 183 (1997).
  • Bruker (2007) APEX2 (Version 2.1-4), SAINT (version 7.34A), SADABS (version 2007/4), BrukerAXS Inc, Madison, Wisconsin, USA.
  • Z. Otwinowsky and W. Minor, Methods in Enzymology; C. W. Carter, Jr. and R. M. Sweet, Eds.; Academic Press: New York, 276, 307 (1997).
  • A. Altomare, C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori and R. Spagna, J. Appl. Crystallogr., 32, 115 (1999).
  • A. Altomare, G. L. Cascarano, C. Giacovazzo and A. Guagliardi, J. Appl. Crystallogr., 26, 343 (1993).
  • G. M. Sheldrick, (1997) SHELXL-97, Program for the Refinement of Crystal Structures. University of Göttingen, Germany.
  • G. M. Sheldrick, Acta Cryst., C71, 3 (2015).
  • S. Mackay, C. Edwards, A. Henderson, C. Gilmore, N. Stewart, K. Shankland, A. Donald, MaXus: a computer program for the solution and refinement of crystal structures from diffraction data. University of Glasgow, Scotland, (1997).
  • D. Waasmaier, A. Kirfel, Acta Crystallog. A., 51, 416 (1995).

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.