Synthesis of D-erythro-sphingosine from D-ribo-phytosphingosine

Bulletin of the Korean Chemical Society

Volumn 30, Issue 3, 2009, Pages 535-536

  Ha, Hyun Joon ^a,b   Yoon, Doo Ha ^a,b   Kang, Lae Sung ^a,b   Hong, Myeng Chan ^c   Lee, Won Koo ^c  

^a Hankuk University of Foreign Studies   (South Korea)

^b Yonsei University   (South Korea)

^c Sogang University   (South Korea)

Author keywords

D erythro sphingosine; D ribo phytosphingosine; Dehydration; Oxazolidin 2 one

Indexed keywords

EID: 70349861404     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2009.30.3.535     Document Type: Article

References (26)

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.
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.
5. Bittmann, R. Chem. Phys. Lipids 2004, 129, 111.
6. Koskinen, P.M.; Koskinen, A.M.P. Synthesis 1998, 1075.
7. Liao, J.; Tao, J.; Lin, G.; Liu, D. Tetrahedron 2005, 61, 4715.
8. Selected publications since 2005 for the syntheses of D-erythro-sphingosine Disadee, W.; Ishikawa, T.J.Org. Chem. 2005, 70, 9399.
9. Chaudhari, V.D.; Kumar, K.S.A.; Dhavale, D.D. Org. Lett. 2005, 7, 5805.
10. Lu, X.; Bittman, R. Tetrahedron Lett. 2005, 46, 1873.
11. Kimenez, P.; Tejero, T.J.Org. Chem. 2006, 71, 4685.
12. Yamamoto, T.; Hasegawa, H.; Hakogi, T.; Katsumura, S. Org. Lett. 2006, 8, 5569.
13. Yang, H.; Liebeskind, L.S. Org. Lett. 2007, 9, 2993.
14. D-ribo-Phytosphingosine [(2S,3S,4R)-2-amino-1,3,4-octadecanetriol] is readily available from a yeast fermentation process. Doosan biotech research center (http://biotech.doosan.co.kr) kindly provided the starting D-ribo-phytosphingosine.
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.
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.
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.
18. Kim, S.; Lee, S.; Lee, T.; Ko, H.; Kim, D.J.Org. Chem. 2006, 71, 8661.
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.
20. Cuadros, R.; Garcini, E.M.; Wandosell, F.; Faircloth, G.; Fernandez-Sousa, J.M.; Avila, J. Cancer Lett. 2000, 152, 23.
21. Yun, J.M.; Sin, T.B.; Hahm, H.S.; Lee, W.K.; Ha, H.-J. J. Org. Chem. 2003, 68, 7675.
22. 4Si: 439.3482, found 439.3477.
23. Engel, P.S.; Schexnayder, M.A. J. Am. Chem. Soc. 1975, 97, 145.
24. Mehta, G.; Murthy, A.N.; Reddy, D.S.; Reddy, A.V. J. Am. Chem. Soc. 1986, 108, 3443.
25. Bunce, R.A.; Schilling III, C.L. J. Org. Chem. 1995, 60, 2748.
26. th ed.; John Wiley & Sons, Inc.: Hoboken, N.J., 2007; p 166.