DOI QR코드

DOI QR Code

Synthesis of D-erythro-Sphingosine from D-ribo-Phytosphingosine

  • Ha, Hyun-Joon (Department of Chemistry and Protein Research Centre for Bio-Industry, Hankuk University of Foreign Studies,Center for Bioactive Molecular Hybrids, Yonsei University) ;
  • Yoon, Doo-Ha (Department of Chemistry and Protein Research Centre for Bio-Industry, Hankuk University of Foreign Studies,Center for Bioactive Molecular Hybrids, Yonsei University) ;
  • Kang, Lae-Sung (Department of Chemistry and Protein Research Centre for Bio-Industry, Hankuk University of Foreign Studies,Center for Bioactive Molecular Hybrids, Yonsei University) ;
  • Hong, Myeng-Chan (Department of Chemistry and Protein Research Centre for Bio-Industry, Hankuk University of Foreign Studies) ;
  • Lee, Won-Koo (Department of Chemistry and Protein Research Centre for Bio-Industry, Hankuk University of Foreign Studies)
  • Published : 2009.03.20

Abstract

Keywords

References

  1. Sweely, C. C. In Biochemistry of Lipids, Lipoproteins, and Membranes; Vance D. E., Vance, J. E., Eds.; Elsevier: Amsterdam, 1991
  2. Kolter, T.; Sandhoff, K. Angew. Chem. Int. Ed. 1999, 38, 1532 https://doi.org/10.1002/(SICI)1521-3773(19990601)38:11<1532::AID-ANIE1532>3.0.CO;2-U
  3. Angel, I.; Bar, A.; Haring, R. Curr. Opin. Drug Disc. Dev. 2002, 5, 728
  4. Kester, M.; Kolesnick, R. Pharmacol. Res. 2003, 47, 365 https://doi.org/10.1016/S1043-6618(03)00048-3
  5. Bittmann, R. Chem. Phys. Lipids 2004, 129, 111 https://doi.org/10.1016/j.chemphyslip.2004.01.004
  6. Koskinen, P. M.; Koskinen, A. M. P. Synthesis 1998, 1075
  7. Liao, J.; Tao, J.; Lin, G.; Liu, D. Tetrahedron 2005, 61, 4715 https://doi.org/10.1016/j.tet.2005.02.075
  8. Disadee, W.; Ishikawa, T. J. Org. Chem. 2005, 70, 9399 https://doi.org/10.1021/jo051495j
  9. Chaudhari, V. D.; Kumar, K. S. A.; Dhavale, D. D. Org. Lett. 2005, 7, 5805 https://doi.org/10.1021/ol052320z
  10. Lu, X.; Bittman, R. Tetrahedron Lett. 2005, 46, 1873 https://doi.org/10.1016/j.tetlet.2005.01.104
  11. Kimenez, P.; Tejero, T. J. Org. Chem. 2006, 71, 4685 https://doi.org/10.1021/jo060465t
  12. Yamamoto, T.; Hasegawa, H.; Hakogi, T.; Katsumura, S. Org. Lett. 2006, 8, 5569 https://doi.org/10.1021/ol062258l
  13. Yang, H.; Liebeskind, L. S. Org. Lett. 2007, 9, 2993 https://doi.org/10.1021/ol070991m
  14. http://biotech.doosan.co.kr
  15. van den Berg, R. J. B. H. N.; Korevaar, C. G. N.; van der Marel, G. A.; Overkleeft, H. S.; van Boom, J. H. Tetrahedron Lett. 2002, 43, 8409 https://doi.org/10.1016/S0040-4039(02)01807-5
  16. Jo, S. Y.; Kim, H. C.; Woo, S. W.; Seo, M. J.; Lee, G.; Kim, H. R. Bull. Kor. Chem. Soc. 2003, 24, 267 https://doi.org/10.5012/bkcs.2003.24.3.267
  17. van den Berg, R. J. B. H. N.; Korevaar, C. G. N.; Overkleeft, H. S.; van der Marel, G. A.; van Boom, J. H. J. Org. Chem. 2004, 69, 5699 https://doi.org/10.1021/jo049277y
  18. Kim, S.; Lee, S.; Lee, T.; Ko, H.; Kim, D. J. Org. Chem. 2006, 71, 8661 https://doi.org/10.1021/jo0614543
  19. Kim, J.; Kim, Y.-W.; Inagakic, Y.; Hwanga, Y.-A.; Mitsutakec, S.; Ryue, Y.-W.; Lee, W. K.; Ha, H.-J.; Park, C.-S.; Igarashi, Y. Bioorg. Med. Chem. 2005, 13, 3475 https://doi.org/10.1016/j.bmc.2005.02.053
  20. Cuadros, R.; Garcini, E. M.; Wandosell, F.; Faircloth, G.; Fernandez-Sousa, J. M.; Avila, J. Cancer Lett. 2000, 152, 23 https://doi.org/10.1016/S0304-3835(99)00428-0
  21. Yun, J. M.; Sin, T. B.; Hahm, H. S.; Lee, W. K.; Ha, H.-J. J. Org. Chem. 2003, 68, 7675 https://doi.org/10.1021/jo034755a
  22. Engel, P. S.; Schexnayder, M. A. J. Am. Chem. Soc. 1975, 97, 145 https://doi.org/10.1021/ja00834a026
  23. Mehta, G.; Murthy, A. N.; Reddy, D. S.; Reddy, A. V. J. Am. Chem. Soc. 1986, 108, 3443 https://doi.org/10.1021/ja00834a026
  24. Bunce, R. A.; Schilling III, C. L. J. Org. Chem. 1995, 60, 2748 https://doi.org/10.1021/ja00272a046
  25. Wuts, P. G. M.; Greene, T. W. Greene's Protective Groups in Organic Synthesis, 4th ed.; John Wiley & Sons, Inc.: Hoboken, N. J., 2007; p 166 https://doi.org/10.1021/jo00114a024

Cited by

  1. A Rapid and Efficient Synthesis of D-erythro-Sphingosine from D-ribo-Phytosphingosine vol.2011, pp.33, 2011, https://doi.org/10.1002/ejoc.201100911
  2. Syntheses of sulfur and selenium analogues of pachastrissamine via double displacements of cyclic sulfate vol.9, pp.20, 2011, https://doi.org/10.1039/c1ob05920c
  3. ChemInform Abstract: Synthesis of D-erythro-Sphingosine from D-ribo-Phytosphingosine. vol.40, pp.32, 2009, https://doi.org/10.1002/chin.200932194
  4. Anti-Selective Dihydroxylation Reactions of Monosubstituted and (E)-Ester Conjugated Allylic Amines by Bulky Alkyl Groups vol.30, pp.5, 2009, https://doi.org/10.5012/bkcs.2009.30.5.1003