New route to enantiomers of cyclic β-hydroxyethers. The crystal structure of (S)-(+)-tetrahydrofurfuryl-O,O'-diacetyl-(2R,3R)-hydrogentartrate

Tetrahedron Asymmetry

Volumn 7, Issue 5, 1996, Pages 1477-1484

  Mravik, András ^a   Böcskei, Zsolt ^b   Keszei, Sándor ^a   Elekes, Ferenc ^a   Fogassy, Elemér ^a  

^a BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

^b Chinoin Pharmaceutical and Chemical Works Ltd   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

TETRAHYDROFURAN DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE;

ARTICLE; CRYSTALLOGRAPHY; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 17344393910     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00165-6     Document Type: Article

References (36)

1. Merz, H.; Stockhaus, K. J. Med. Chem. 1979, 22, 1475-1483.
2. Merz, H.; Stockhaus, K.; Wick, H. J. Med. Chem. 1975, 18, 996-1000.
3. a) Alajarin, R.; Vaquero, J. J.; Alvarez-Builla, J.; Pastor, M.; Sunkel, C.; Fau de Casa-Juana, M.; Priego, J.; Statkow, P. R.; Sanz-Aparicio, J.; Fonseca, I. J. Med. Chem. 1995, 38, 2830-2841;
4. b) Alajarin, R.; Alvarez-Builla, J.; Vaquero, J. J.; Sunkel, C.; Fau de Casa-Juana, M.; Statkov, P. R.; Sanz-Aparicio, J. Tetrahedron: Asymmetry 1993, 4, 617-620;
5. c) Franckowiak, G.; Bechem, M.; Schramm, M.; Thomas, G. Eur. J. Pharmacol. 1985, 114, 223-226.
6. Ebata, T.; Kawakami, M.; Koseki, Y.; Matsushita, H. Agric. Biol. Chem. 1991, 55, 1685.
7. Ebata, T.; Koseki, Y.; Kawakami, M.; Matsushita, H. JP 03 167, 180 1991 [C.A.: 116, 41288 (1991)].
8. Whitesell, J. K.; Jaw, B.-R. J. Org. Chem. 1981, 46, 2798-2799.
9. Gagnaire, D.; Butt, A. Bull. Soc. Chim. Fr. 1961, 309-312.
10. Gagnaire, D.; Butt, A. Bull. Soc. Chim. Fr. 1961, 312-317.
11. Ingersoll, A. W. The resolution of alcohols. In Organic Reactions Vol. 2.; Adams, R. Ed.; John Wiley and Sons, Inc.: New York, 1947; chapter 9, pp. 376-414.
12. Balfe, M. P.; Irwin, M.; Kenyon, J. J. Chem. Soc. 1941, 312-316.
13. Descours, D.; Fedstal, D.; Leger, J. M.; Carpy, A. Helv. Chim. Acta 1991, 74, 1757-1763.
14. Hartman, F. C.; Barker, R. J. Org. Chem. 1964, 29, 873-877.
15. Cervinka, O.; Bajanzulyn, O.; Fábriová, A.; Šackus, A. Collect. Czech. Chem. Commun. 1986, 51, 404-407.
16. Toda, F. JP 62 201,879 1987 [C.A.: 110, 57491, (1989)].
17. Ladner, W. E.; Whitesides, G. M. J. Am. Chem. Soc. 1984, 106, 7250-7251.
18. Lemieux, R. U.; Martin, J. C. Carbohyd. Res. 1970, 13, 139-161.
19. Mravik, A. Unpublished results.
20. Mravik, A.; Fogassy, E.; Lepp, Zs. Hung. Pat. Appl. P00185 1996.
21. a) Lucas, H. J.; Baumgarten, W. J. Am. Chem. Soc. 1941, 63, 1653-1657;
22. b) Uray, G.; Lindner, W. Tetrahedron 1988, 44, 4357-4362.
23. a) Bell, K. H. Aust. J. Chem. 1979, 32, 65-70;
24. b) Bell, K. H. Aust. J. Chem. 1979, 32, 2625-2629;
25. c) Bell, K. H. Aust. J. Chem. 1981, 34, 671-673.
26. Palmer, R. J.; Stirling, J. M J. Am. Chem. Soc. 1980, 102, 7888-7892.
27. Jeromin, G. E. Ger. Offen DE 4 009 891 1991 [C.A.: 116, 127005 (1991)].
28. Defaye, J.; Naumberg, M.; Reyners, T. J. Heterocycl. Chem. 1969, 6, 229-234.
29. a) Abbot, E. B.; McKenzie, A.; Ross, J. D. McBeath Chem. Ber. 1938, 71, 16-27;
30. b) Kolasa, T.; Miller, M. J. Tetrahedron 1989, 45, 3071-3080.
31. Beutel, R.; Tishler, M. J. Am. Chem. Soc. 1946, 68, 1463-1465.
32. Kivikoski, J.; Vepsäläinen, J.; Suontamo, R.; Pohjala, E.; Laatikainen, R. Tetrahedron: Asymmetry 1993, 4, 709-722.
33. Molecular Structure Corporation (1992) teXsan: Crystal Structure Analysis Package.
34. Sheldrick, G. M. (1993) SHELXL-93 Program for crystal structure refinement.
35. Chattaway, F. D.; Parkes, G. D. J. Chem. Soc. 1923, 123, 663-669.
36. Austin, P. C.; Park, J. R. J. Chem. Soc. 1925, 127, 1926-1934.