The Correct Structures of "Dihydrothiamine". Resolution of a Long-Standing Controversy

Journal of Organic Chemistry

Volumn 62, Issue 20, 1997, Pages 6760-6766

  Zoltewicz, John A ^a   Dill, Carlton D ^a   Abboud, Khalil A ^a  

^a University of Florida ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIHYDROTHIAMINE; SODIUM BOROHYDRIDE; THIAMINE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CHIRALITY; CRYSTAL STRUCTURE; DIASTEREOISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0030843324     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970782n     Document Type: Article

References (38)

1. Zoltewicz, J. A.; Uray, G. Bioorg. Chem. 1994, 22, 1.
2. Compounds reported in the literature are conveniently identified by their melting points.
3. Karrer, P.; Krishna, H. Helv, Chim. Acta 1950, 33, 555.
4. Karrer, P.; Krishna, H. Helv. Chim. Acta 1952, 35, 459.
5. Bonvicino, G. E.; Hennessy, D. J. J. Am. Chem. Soc. 1957, 79, 6325.
6. Iwatsu, T. Yakugaku Zasshi 1955, 75, 677.
7. Matsukawa, T.; Hirano, H.; Iwatsu, T.; Yurugi, S. J. Vitaminol. 1957, 3, 213.
8. Matsukawa, T.; Hirano, H.; Iwatsu, T.; Yurugi, S. J. Vitaminol. 1957, 3, 218.
9. Matsukawa, T.; Iwatsu, T. J. Vitaminol. 1955, 1, 305.
10. Hirano, H.; Iwatsu, T.; Yurugi, S. Yakugaku Zasshi 1957, 77, 241.
11. Beilsteins Handbuch der Organische Chemie, Supplement III/ IV, Vol. 27/3; Springer-Verlag: New York, 1983.
12. Hirano, H. Yakugaku Zasshi 1958, 78, 1387.
13. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; J. Wiley & Sons: New York, 1994.
14. Etter, M. C. Acc. Chem. Res. 1990, 23, 120.
15. Takamizawa, A.; Hirai, K.; Ishiba, T.; Makino, I. Chem. Pharm. Bull. 1971, 19, 759.
16. Siro, M.; Nakai, H.; Makino, I.; Takamizawa, A. Acta Crystallogr. 1978, B34, 3424.
17. Kemp, D. S.; O'Brien, J. T. J. Am. Chem. Soc. 1970, 92, 2554.
18. Clarke, G. M.; Sykes, P. J. Chem. Soc. 1967, 1411.
19. Leeper, F. J.; Lowe, P. N. Heterocycles 1983, 20, 65.
20. Bau, R.; Hyun, Y.-S.; Lim, J.; Choi, H.; Yannopoulos, A.; Hadjiliadis, N. Inorg. Chim. Acta 1988, 150, 107.
21. Brown, H. C.; Bell, H. M. J. Org. Chem. 1962, 27, 1928.
22. Schlesinger, H. I.; Brown, H. C.; Hoekstra, H. R.; Rapp, L. R. J. Am. Chem. Soc. 1953, 75, 199.
23. Lane, C. F. Synthesis 1975, 135.
24. Maier, G. D.; Metzler, D. E. J. Am. Chem. Soc, 1957, 79, 4387.
25. Chahine, J. M. E. H.; Dubois, J. E. J. Chem. Soc., Perkin Trans, 2 1989, 25.
26. Chahine, J. M. E. H. J. Chem, Soc., Perkin Trans. 2 1990, 1045.
27. Washabaugh, M. W.; Yang, C. C.; Hollenbach, A. D.; Chen, P. Bioorg. Chem. 1993, 21, 170.
28. Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183.
29. Cain, A. H.; Sullivan, G. R.; Roberts, J. D. J. Am. Ckem. Soc. 1977, 99, 6423.
30. Schellenberger, A. Angew. Chem., Int. Ed. Engl. 1967, 6, 1024.
31. Schellenberger, A. Chem. Ber. 1990, 723, 1489.
32. Crabb, T. A.; Katritzky, A. R. Adv. Heterocycl. Chem. 1984, 36.
33. Hadjiliadis, N.; Markopoulos, J. J. Chem. Soc., Dalton Trans, 1981, 1635.
34. Risinger, G. E.; Breaux, E. J.; Hsieh, H. H. J. Chem. Soc., Chem. Commun. 1968, 841.
35. Sorensen, H. C.; Ingraham, L. L. Biochim. Biophys. Acta 1970, 208, 343.
36. Sorensen, H. C.; Ingraham, L. L. J. Heterocycl. Chem. 1970, 7, 711.
37. Moorthy, P. N.; Haynon, E. J. Org. Chem. 1977, 42, 879.
38. Sheldrick, G. M. 1995, SHELXTL5. Siemens Analytical Instrumentation. Madison, WI.