Direct synthesis of plasmenylcholine from allyl-substituted glycerols

Journal of Organic Chemistry

Volumn 68, Issue 17, 2003, Pages 6760-6766

  Shin, Junhwa ^a   Thompson, David H ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FACILE PREPARATION;

ETHERS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

GLYCEROL;

1 ALLYLGLYCEROL; 1,3 DIOXOLANE DERIVATIVE; 4 HYDROXYMETHYL 2,2 DIMETHYL 1,3 DIOXOLANE; ALLYL COMPOUND; CHOLINE DERIVATIVE; GLYCEROL; GLYCEROL ETHER; PLASMALOGEN; PLASMENYLCHOLINE; SILANE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; LOW TEMPERATURE; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

GLYCEROL; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; PLASMALOGENS;

EID: 0043010906     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026826w     Document Type: Article

References (43)

1. Lee, T.-c. Biochim. Biophys. Acta 1998, 1394, 129-145.
2. Sugiura, T.; Waku, K. In Platelet Activating Factor and Related Lipid Mediators; Snyder, F., Ed.; Plenum Press: New York, 1987; pp 55-85.
3. Fonteh, A. N.; Chilton, F. H. J. Immunol. 1992, 148, 1784-1791.
4. Snyder, F.; Lee, T.-c.; Blank, M. L. In Advances in Lipobiology; Gross, R. W., Ed.; JAI Press: Stamford, CT, 1997; Vol. 2, pp 261-286.
5. Glaser, P. E.; Gross, R. W. Biochemistry 1994, 33, 5805-5812.
6. Thompson, D. H.; Gerasimov, O. V.; Wheeler, J. J.; Rui, Y.; Anderson, V. C. Biochim. Biophys. Acta 1996, 1279, 25-34.
7. Murphy, R. C. Chem. Res. Toxicol. 2001, 14, 463-472.
8. (a) Gerasimov, O. V.; Schwan, A.; Thompson, D. H. Biochim. Biophys. Acta 1997, 1324, 200-214.
9. (b) Rui, Y.; Wang, S.; Low, P. S.; Thompson, D. H. J. Am. Chem. Soc. 1998, 120, 11213-11218.
10. (c) Gerasimov, O. V.; Boomer, J. A.; Qualls, M. M.; Thompson, D. H. Adv. Drug. Deliv. Rev. 1999, 38, 317-338.
11. (d) Wymer, N. J.; Gerasimov, O. V.; Thompson, D. H. Bioconjug. Chem. 1998, 9, 305-308.
12. (e) Qualls, M. M.; Thompson, D. H. Int. J. Cancer 2001, 93, 384-392.
13. (f) Collier, J. H.; Hu, B. H.; Ruberti, J. W.; Zhang, J.; Shum, P.; Thompson, D. H.; Messersmith, P. B. J. Am. Chem. Soc. 2001, 123, 9463-9464.
14. (g) Boomer, J. A.; Thompson, D. H.; Sullivan, S. Pharm. Res. 2002, 19, 1292-301.
15. Rui, Y.; Thompson, D. H. Chem. Eur. J. 1996, 2, 1505-1508.
16. Qin, D. H.; Byun, H. S.; Bittman, R. J. Am. Chem. Soc. 1999, 121, 662-668.
17. Shin, J.; Qualls, M. M.; Boomer, J. A.; Robarge, J.; Thompson, D. H. J. Am. Chem. Soc. 2001, 123, 508-509.
18. Shin, J.; Gerasimov, O. V.; Thompson, D. H. J. Org. Chem. 2002, 67, 6503-6508.
19. Dodd, G. H.; Golding, B. T.; Ioannou, P. V. J. Chem. Soc., Chem. Commun. 1975, 249-250.
20. van Lohuizen, O. E.; Verkade, P. E. Rec. Trav. Chim. Pays-Bas 1960, 79, 133-159.
21. Migration can occur during chromatography on silica gel: Pfaendler, H. R.; Weimar, V. Synthesis 1996, 1345-1349.
22. Crossley, A.; Freeman, I. P.; Hudson, B. J. F.; Pierce, J. H. J. Chem. Soc. 1959, 760-764.
23. (a) Craig, J. C.; Hamon, D. P. G.; Brewer, H. W.; Harle, H. J. Org. Chem. 1965, 30, 907-910.
24. (b) Piantadosi, C. F.; Hirsch, A. F.; Yarbro, C. L.; Anderson, C. E. J. Org. Chem. 1963, 28, 2425-2428.
25. (c) Titov, V. I.; Serebrennikova, G. A.; Preobrazhenskii, N. A. Zh. Org. Khim. 1970, 6, 1154-1159; Chem. Abstr. 1970, 73, 65983z;
26. (c) Titov, V. I.; Serebrennikova, G. A.; Preobrazhenskii, N. A. Zh. Org. Khim. 1970, 6, 1154-1159; Chem. Abstr. 1970, 73, 65983z;
27. (d) Gigg, J.; Gigg, R. J. Chem. Soc., (C) 1968, 16-21.
28. (e) Vtorov, I. B.; Serebrennikova, G. A.; Evstigneeva, R. P. Tetrahedron Lett. 1971, 48, 4605-4608.
29. (f) de Wit, P. P.; van der Steeg, M.; van der Gen, A. Rec. Trav. Chim. Pays-Bas. 1985, 104, 307-308.
30. (g) Slotboom, A. J.; De Haas, G. H.; Van Deenen, L. L. M. Chem. Phys. Lipids 1967, 1, 192-208.
31. (h) Chebyshev, A. V.; Serebrennikova, G. A.; Evstigneeva, R. P. Zh. Org. Khim. 1977, 13, 703-709; Chem. Abstr. 1977, 87, 38790s.
32. (h) Chebyshev, A. V.; Serebrennikova, G. A.; Evstigneeva, R. P. Zh. Org. Khim. 1977, 13, 703-709; Chem. Abstr. 1977, 87, 38790s.
33. (i) Pfaendler, H. R.; Muller, F. X. Synthesis 1992, 350-352.
34. Gil, J. F.; Ramon, D. J.; Yus, M. Tetrahedron 1994, 50, 3437-3446.
35. Still, W. C.; Macdonald, T. L. J. Am. Chem. Soc. 1974, 96, 5561-5563.
36. Guibe, F. Tetrahedron 1997, 53, 13509-13556.
37. Katritzky, A. R.; Piffl, M.; Lang, H.; Anders, E. Chem. Rev. 1999, 99, 665-722.
38. Evans, D. A.; Andrews, G.; Buckwalter, B. J. Am. Chem. Soc 1974, 96, 5560-5561.
39. Yanagisawa, A.; Yasue, K.; Yamamoto, H. Synlett 1993, 686-688.
40. Tomooka, K.; Inoue, T.; Nakai, T. Chem. Lett. 2000, 418-419.
41. Trost, B. M.; Latimer, L. H. J. Org. Chem. 1977, 42, 3212-3214.
42. Greene, T. W.; Wuts, P. G. M. Protective groups in organic synthesis, 3rd ed.; Wiley: New York, 1999.
43. Gupta, C. M.; Radhakrishnan, R.; Khorana, H. G. Proc. Natl. Acad. Sci. U.S.A. 1977, 74, 4315-4319.