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Efficient Synthesis of 2(S)-[1(S)-Azido-2-phenylethyl]oxirane

  • Published : 2008.05.20
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Abstract

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References

  1. Power, M. D.; Marx, P. A.; Bryant, M. L.; Gardner, M. B.; Barr, P. J.; Luciw, P. A. Science 1986, 231, 1567 https://doi.org/10.1126/science.3006247
  2. Kempf, D. J.; Marsh, K. C.; Denissen, J. F.; McDonald, E.; Vasavononda, S.; Flentge, C. A.; Green, B. G.; Fino, L.; Park, C. H.; Kong, X.-P.; Wideburg, N. E.; Saldivar, A.; Ruiz, L.; Kati, W. M.; Sham, H. L.; Robins, T.; Stewart, K. D.; Hsu, A.; Plattner, J. J.; Leonard, J.; Norbeck, D. Pro. Natl. Acad. Sci. U.S.A. 1995, 92, 2484 https://doi.org/10.1073/pnas.92.7.2484
  3. Flexner, C. New Engl. J. Med. 1998, 338, 1281 https://doi.org/10.1056/NEJM199804303381808
  4. Roberts, N. A.; Martin, J. A.; Kinchington, D.; Broadhurst, A. V.; Craig, J. C.; Duncan, I. B.; Galphin, S. A.; Handa, B. K.; Krohn, A.; Lambert, R. W.; Merrett, J. H.; Mills, J. S.; Parkes, K. E. B.; Redshaw, S.; Ritchie, A. J.; Taylor, D. L.; Thomas, G. J.; Machin, P. J. Science 1990, 248, 358 https://doi.org/10.1126/science.2183354
  5. Kim, E. E.; Baker, C. T.; Dwyer, M. D.; Murcko, M. A.; Rao, B. G.; Tung, R. D.; Navia, M. A. J. Am. Chem. Soc. 1995, 117, 1181 https://doi.org/10.1021/ja00108a056
  6. Kaldor, S. W.; Kalish, V. J.; Davies, J. F.; Shetty, B. V.; Fritz, J. E.; Appelt, K.; Burgess, J. A.; Campanale, K. M.; Chirgadze, N. Y.; Clawson, D. K.; Dressman, B. A.; Hatch, S. D.; Khalil, D. A.; Kosa, M. S.; Tatlock, J. H. J. Med. Chem 1997, 40, 3979 https://doi.org/10.1021/jm9704098
  7. Pearl, L. H.; Taylor, W. R. Nature 1987, 329, 351. (b) Huff, J. R. J. Med. Chem. 1991, 34, 2305 https://doi.org/10.1021/jm00112a001
  8. Parkes, K. E. B.; Bushnell, D. J.; Cracjeff, P. H.; Dunsdon, S. J.; Freeman, A. C.; Gunn, M. P.; Popkins, R. A.; Lambert, R. W.; Thomas, G. J. J. Org. Chem. 1994, 59, 3656 https://doi.org/10.1021/jo00092a026
  9. Beaulieu, P. L.; Wernic, D. J. Org. Chem. 1996, 61, 3635 https://doi.org/10.1021/jo960109i
  10. Rieger, D. L. J. Org. Chem. 1997, 62, 8546 https://doi.org/10.1021/jo9705778
  11. Corey, E. J.; Zhang, F.-Y. Angew. Chem. Int. Ed. 1999, 38, 1931 https://doi.org/10.1002/(SICI)1521-3773(19990712)38:13/14<1931::AID-ANIE1931>3.0.CO;2-4
  12. Zook, S. E.; Busse, J. K.; Borer, B. C. Tetrahedron Lett. 2000, 41, 7017 https://doi.org/10.1016/S0040-4039(00)01231-4
  13. Tomasselli, A. G.; Heinrikson, R. L. Biochim. Biophys. Acta 2000, 189
  14. Rocheblave, L.; Bihel, F.; Michelis, C.; Priem, G.; Courcambeck, J.; Bonnet, B.; Chermann, J.-C.; Kraus, J.-L. J. Med. Chem. 2002, 45, 3321 https://doi.org/10.1021/jm0208323
  15. Yanada, R.; Koh, Y.; Nishimori, N.; Matsumura, A.; Obika, S.; Mitsuya, H.; Fujii, N.; Takemoto, Y. J. Org. Chem. 2004, 69, 2417 https://doi.org/10.1021/jo035482m
  16. Honda, Y.; Katayama, S.; Kojima, M.; Suzuki, T.; Kishibata, N.; Izawa, K. Org. Biomol. Chem. 2004, 2, 2061 https://doi.org/10.1039/b404071f
  17. Luly, J. R.; Dellaria, J. F.; Plattener, J. J.; Soderquist, J. L.; Yi, N. J. Org. Chem. 1987, 52, 1487 https://doi.org/10.1021/jo00384a020
  18. Ghosh, A. K.; McKee, S. P.; Lee, H. Y.; Thompson, W. J. Chem. Soc. Chem. Commun. 1992, 273
  19. Kim, B. M.; Bae, S. J.; So, S. M.; Yoo, H. T.; Chang, S. K.; Lee, J. H.; Kang, J. Org. Lett. 2001, 3, 2349 https://doi.org/10.1021/ol016147s
  20. Abushanab, E.; Vmishetti, P.; Leiby, R. W.; Singh, H. K.; Mikkilineni, A. B.; Wu, D. C.-J.; Saibaba, R.; Panzica, R. P. J. Org. Chem. 1988, 53, 2598 https://doi.org/10.1021/jo00246a037
  21. Greenberg, S.; Moffat, G. J. J. Am. Chem. Soc. 1973, 95, 4016 https://doi.org/10.1021/ja00793a031

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