Synthesis of glycosyl glycerols and related glycolipids

Journal of Carbohydrate Chemistry

Volumn 17, Issue 6, 1998, Pages 937-968

  Suhr, René ^a   Scheel, Oliver ^b   Thiem, Joachim ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

^b BEIERSDORF AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0032396196     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328309808007465     Document Type: Article

References (61)

1. H. Colin and E. Guéguen, Compt. Rend., 191, 163 (1930).
2. H. Colin and J. Augier, Compt. Rend. 195, 1042 (1933).
3. IUPAC-IUB Commission on Biochemical Nomenclature, The Nomenclature of Lipids, Biochem. Biophys. Acta, 152, 1 (1968).
4. E. W. Putman and W. Z. Hassid, J. Am. Chem. Soc., 76, 2221 (1954).
5. M. Kaneda, K. Mizutani, Y. Takahashi, G. Kurono and Y. Nishikawa, Tetrahedron Lett., 45, 3937 (1974).
6. H. Shimomura, Y. Sashida, Y. Mimaki, Y. Kudo and K. Maeda, Chem. Pharm. Bull., 36, 12, 4841 (1988).
7. J.-A. Pocard, L. Tombras Smith, G. M. Smith and D. Le Rudulier, J. Bacteriol., 176, 22, 6877 (1994).
8. M. A. Mackay, R. S. Norton and L. J. Borowitzka, J. Biol. Chem., 130, 2177 (1984).
9. R. H. Reed, L. S. Borowitzka, M. A. Mackay, J. A. Chudek, R. Foster, S. R. C. Warr, D. J. Moore and W. D. P. Stewart, FEMS Microbiol. Rev., 39, 51 (1986).
10. R. H. Reed and W. D. P. Stewart, Marine Biol., 88, 1 (1985).
11. S. R. Warr, R. H. Reed and W. D. P. Stewart, J. Gen. Microbiol., 130, 2169 (1984).
12. N. Erdmann, C. Berg and M. Hagemann, Arch. Hydrobiol., 114, 521 (1989).
13. M. Hagemann and E. Zuther, Arch. Microbiol., 158, 429 (1992).
14. U. Karsten, K. D. Barrow and R. J. King, Plant. Physiol., 103, 485 (1993).
15. O. Scheel, Dissertation, University of Hamburg (1996).
16. O. Scheel, J. Thiem and G. Schneider, Pat. Appl. DE: 195.40.749 (1995); Chem. Abstr., 127, 23498y (1997).
17. O. Scheel, J. Thiem and G. Schneider, Pat. Appl. DE: 195.40.749 (1995); Chem. Abstr., 127, 23498y (1997).
18. E. Heinz, Plant Glycolipids: Structure, Isolation and Analysis, Adv. Lipid Method., 3, 211 (1996)
19. J. Joyard, M. A. Block and R. Douce, Eur. J. Biochem., 199, 489 (1991).
20. M. S. Webb and B. R. Green, Biochim. Biophys. Acta, 1060, 133 (1991).
21. H. Carter, R. H. McCluer and E. D. Slifer, J. Am. Chem. Soc., 78, 3735 (1956).
22. R. H. Gigg, Chem. Phys. Lipids, 26, 287 (1980).
23. R. P. Evstigneeva, A. V. Lyubeshkin, M. V. Anikin and Yu. L. Sebyakin, Dokl. Chem. (Engl. Transl.), 330, 119 (1993).
24. J. Dahmén, T. Frejd, G. Magnusson and G. Noori, Carbohydr. Res., 114, 328 (1983)
25. W. Klotz and R. R. Schmidt, Liebigs Ann. Chem., 683 (1993).
26. B. Helferich and D. V. Kashelikar, Chem. Ber., 90, 2094 (1957).
27. J. M. Vega-Pérez, E. Blanco, M. Trujillo, M. Vega and F. Iglesias-Guerra, Ninth European Carbohydrate Symposium, Utrecht 1997, Abstr. A6.
28. J. K. Fairweather, R. V. Stick and D. M. G. Tilbrook, Ninth European Carbohydrate Symposium, Utrecht 1997, Abstr. A27.
29. E. Falent-Kwast, P. Kovác, A. Bax and C. P. J. Glaudemans, Carbohydr. Res., 145, 332 (1986).
30. F. Björkling and S.E. Godtfredsen, Tetrahedron, 44, 2957 (1988)
31. R. Tamura, T. Ushio, H. Takahashi, K. Nakamura, N. Azuma, F. Toda and K. Endo, Chirality, 9, 220 (1997).
32. R. P. Hanzlik and M. Leinwetter, J. Org. Chem., 43, 3, 438 (1978).
33. G. Stoll (Henkel K.-G. A.), Eur. Pat. Appl. EP 341548; Chem. Abstr., 112, 237236a (1990).
34. G. Stoll (Henkel K.-G. A.), Eur. Pat. Appl. EP 341548; Chem. Abstr., 112, 237236a (1990).
35. A. Fairbourne, G. P. Gibson and D.-W. Stephens, J. Chem. Soc., 133, 445 (1931).
36. F. M. Albini, C. Murelli, G. Patritti and M. Rovati, Synth. Commun., 24, 1651 (1994).
37. P. Karrer and O. Hurwitz, Helv. Chim. Acta, 5, 864 (1922).
38. C. Piantadosi, C. E. Anderson, E. A. Brecht and C. L. Yarbro, J. Am. Chem. Soc., 80, 6613 (1958).
39. N. M. Carter, Ber. Dtsch. Chem. Ges., 63, 1684 (1930).
40. V. K. Srivastava, Carbohydr. Res., 103, 286 (1982).
41. W. P. Stöckl and H. Weidmann, J. Carbohydr. Chem., 8, 169 (1989).
42. Y. Pomeranz and H. P. Wehrli, Food Technol., 23, 9, 1213 (1969).
43. A. I. Bashkatova, G. V. Smirnova, V. I. Shvets and R. P. Evstigneeva, Zh. Org. Khim., 6, 1756 (1970); Chem. Abstr., 73, 110072q (1970).
44. A. I. Bashkatova, G. V. Smirnova, V. I. Shvets and R. P. Evstigneeva, Zh. Org. Khim., 6, 1756 (1970); Chem. Abstr., 73, 110072q (1970).
45. A. I. Bashkatova, G. V. Smirnova, V. I. Shvets and R. P. Evstigneeva, Zh. Org. Khim., 7, 1644 (1971); Chem. Abstr., 75, 152043c (1971).
46. A. I. Bashkatova, G. V. Smirnova, V. I. Shvets and R. P. Evstigneeva, Zh. Org. Khim., 7, 1644 (1971); Chem. Abstr., 75, 152043c (1971).
47. D. A. Mannock, R. N. Lewis and R. N. McElhaney, Chem. Phys. Lipids, 43, 113 (1987).
48. H. P. Wehrli and Y. Pomeranz, US Pat. 3 729.461, Chem. Abstr., 78, 160068 (1973).
49. H. P. Wehrli and Y. Pomeranz, US Pat. 3 729.461, Chem. Abstr., 78, 160068 (1973).
50. P. W. Austin, F. E. Hardy, J. G. Buchanan and J. Baddiley, J. Chem. Soc., 2128 (1964).
51. R. R. Schmidt and W. Kinzy, Adv. Carbohydr. Chem. Biochem., 50, 21 (1994).
52. The diastereomer formed in a minor amount is labeled I, the other one II, diastereomeric ratio for 12: I/II = 0.82:1; for 13: I/II = 0.72:1; for 14: I/II = 0.82:1.
53. R. C. Beier, B. P. Bradford and G. A. Strobel, Carbohydr. Res., 93, 141 (1981).
54. O. Jesudason, J. Chem. Soc., Perkin Trans. 1, 1443 (1974)
55. A. I. Bashkatova, G. V. Smirnova, V. N. Volynskaya, V. I. Shvets and R. P. Evstigneeva, Zhur. Org. Khim., 9, 1393 (1973); J. Org. Chem. U.S.S.R., 9, 1422 (1973).
56. A. I. Bashkatova, G. V. Smirnova, V. N. Volynskaya, V. I. Shvets and R. P. Evstigneeva, Zhur. Org. Khim., 9, 1393 (1973); J. Org. Chem. U.S.S.R., 9, 1422 (1973).
57. A. P. Kaplun, V. I. Shvets and R. P. Evstigneeva, Bioorg. Khim., 3, 222 (1977); J. Bioorg. Chem. U.S.S.R., 3, 165 (1977).
58. A. P. Kaplun, V. I. Shvets and R. P. Evstigneeva, Bioorg. Khim., 3, 222 (1977); J. Bioorg. Chem. U.S.S.R., 3, 165 (1977).
59. D. E. Brundish and J. Baddiley, Carbohydr. Res., 8, 308 (1968).
60. P. W. Austin, F. E. Hardy, J. G. Buchanan and J. Baddiley, J. Chem. Soc., 1419 (1965).
61. A. J. Charlson, P. A. J. Gorin and A. S. Perlin, Can. J. Chem., 34, 1811 (1956).