A short and efficient stereoselective synthesis of dihydrosphingosine triacetate

Tetrahedron Asymmetry

Volumn 10, Issue 24, 1999, Pages 4797-4802

  Fernandes, Rodney A ^a   Kumar, Pradeep ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

SPHINGANINE; SULFITE;

ACETYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROXYLATION; MASS SPECTROMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033370162     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00578-9     Document Type: Article

References (37)

1. Hannun, Y. A.; Bell, R. M. Science 1989, 243, 500-507.
2. Schwartz, G. K.; Jiang, J.; Kelsen, D.; Albino, A. P. J. Nat. Cancer Inst. 1993, 85, 402-407.
3. Sibuya, A.; Kawashima, K.; Ikeda, M.; Kitawaga, I. Tetrahedron Lett. 1989, 30, 7205-7208.
4. (a) Kumar, P.; Schmidt, R. R. Synthesis 1998, 33-35.
5. (b) Schmidt, R. R. In Synthesis in Lipid Chemistry; Tyman, J. H. P., Ed.; Royal Society of Chemistry: Cambridge, UK; 1996, pp. 93-118 and references cited therein.
6. (c) Murakami, T.; Hato, M. J. Chem. Soc., Perkin Trans. 1 1996, 823-827.
7. (d) Li, Y.-L.; Wu, Y.-L. Liebigs Ann. Chem. 1996, 2079-2082.
8. (e) Schmidt, R. R.; Bar, T.; Wild, R. Synthesis 1995, 868-876.
9. (f) Wild, R.; Schimdt, R. R. Liebigs Ann. Chem. 1995, 755-764.
10. (g) Hirata, N.; Yamagiwa, Y.; Kamikawa, T. J. Chem. Soc., Perkin Trans, 1 1991, 2279-2280.
11. (a) Villard, R.; Fotiadu, F.; Buono, G. Tetrahedron: Asymmetry 1998, 9, 607-611.
12. (b) Dondoni, A.; Perrone, D.; Turturici, E. J. Chem. Soc., Perkin Trans. 1 1997, 2389-2393.
13. (c) Williams, L.; Zhang, Z.; Shao, F.; Carroll, P.; Joullie, M. M. Tetrahedron 1996, 52, 11673-11694.
14. (d) Soai, K.; Takahashi, K. J. Chem. Soc., Perkin Trans. 1 1994, 1257-1258.
15. (e) Herold, P. Helv. Chim. Acta 1988, 71, 354-362.
16. (f) Nimkar, S.; Menaldino, D.; Merrill, A. H.; Liotta, D. Tetrahedron Lett. 1988, 29, 3037-3040.
17. (g) Garner, P.; Park, J. M.; Malecki, E. J. J. Org. Chem. 1988, 53, 4395-4398.
18. (a) Spanu, P.; Rassu, G.; Pinna, L.; Battistini, L.; Casiraghi, G. Tetrahedron: Asymmetry 1997, 8, 3237-3243.
19. (b) Davis, F. A.; Reddy, G. V. Tetrahedron Lett. 1996, 37, 4349-4352.
20. (c) Katsumura, S.; Yamamoto, N.; Fukuda, E.; Iwama, S. Chem. Lett. 1995, 393-394 and references cited therein.
21. (a) Bongini, A.; Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. J. Chem. Soc., Perkin Trans. 1 1986, 1339-1344.
22. (b) Mori, K.; Umemura, T. Tetrahedron Lett. 1982, 23, 3391-3394.
23. (c) Mori, K.; Umemura, T. Tetrahedron Lett. 1981, 22, 4433-4436.
24. (d) Reist, E. J.; Christie, P. H. J. Org. Chem. 1970, 35, 3521-3524, 4127-4128.
25. (e) Carter, H. E.; Shapiro, D. J. Am. Chem. Soc. 1953, 75, 5131-5132.
26. (f) Jenny, E. F.; Grob, C. A. Helv. Chim. Acta 1953, 36, 1936-1944.
27. (g) Grob, C. A.; Jenny, E. F.; Utzinger, H. Helv. Chim. Acta 1951, 34, 2249-2254.
28. (a) Pais, G. C. G.; Fernandes, R. A.; Kumar, P. Tetrahedron 1999, 55, 13445-13450.
29. (b) Fernandes, R. A.; Kumar, P. Tetrahedron: Asymmetry 1999, 10, 4349-4356.
30. (c) Kumar, P.; Saravanan, K. Tetrahedron 1998, 54, 2161-2168.
31. (a) Tietze, L. F.; Golitzer, J. Synthesis 1998, 873-878.
32. (b) Becker, H.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 448-451.
33. (c) Torii, S.; Liu, P.; Bhuvaneswari, N.; Amatore, C.; Jutand, A. J. Org. Chem. 1996, 61, 3055-3060.
34. (d) For a review on asymmetric dihydroxylation, see: Kolb, H. C.; VanNiewenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
35. For the measurement of enantiomeric excess, the diol 5 was converted into its dibenzoate 9. The enantiomeric purity of the dibenzoate 9 was estimated to be in excess of 99% by HPLC using Lichrocart 250-4 (4mm IDx25cm) HPLC-Cartridge (R.R.-Whelk-01), 10% iPrOH in hexane, 1 mL/min. (Matrix Presented)
36. For a review on cyclic sulfites and sulfates, see: Lohray, B. B. Synthesis 1992, 1035-1052.
37. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; Harper & Row: New York, 1987; p. 321 and references cited therein.