On the stereochemical purity of (+)-7-aminocephalosporanic acid

Tetrahedron

Volumn 52, Issue 22, 1996, Pages 7691-7702

  Oberhauser, Thomas ^a   Meduna, Vladimir ^a  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

7 AMINOCEPHALOSPORANIC ACID;

ARTICLE; CIS TRANS ISOMERISM; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMERISM; PRIORITY JOURNAL; STEREOISOMERISM;

EID: 0029892486     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)00353-5     Document Type: Article

References (29)

1. (a) Fechtig, B.; Peter, H.; Bickel, H.; Vischer, E. Helv. Chim. Acta 1968, 57, 1108-1119.
2. (b) Hatfield, L.D.; Lunn, W.H.W.; Jackson, B.G.; Peters, L.R.; Blaszczak, L.C.; Fisher, J.W.; Gardner, J.P.; Dunigan, J.M. Recent Advances in the Chemistry of β-Lactam Antibiotics, (Ed. Gregory, G.I.), The Royal Chemical Society, London, 1981, pp. 109-124.
3. Abraham, E.P.; Newton, G.G.F. Biochem. J. 1961, 79, 377-393.
4. Hodgkin, D.C.; Maslen, E.N. Biochem. J. 1961, 79, 393-402.
5. Woodward, R.B.; Heusler, K.; Gosteli, J.; Naegeli, P.; Oppolzer, W.; Ramage, R.; Ranganathan, S.; Vorbrüggen, H. J. Am. Chem. Soc. 1966, 88, 852-853.
6. Sweet, R.M.; Dahl, L.F. J. Am. Chem. Soc. 1970, 92, 5489-5507.
7. (a) Paulus, E.F. Acta Cryst. 1974, B30, 2918-2920.
8. (b) Simon, K.; Agary, G.; Jászberényi, J.C.; Gunda, T.E.; Bognár, R. J. Mol. Struct. 1983, 99, 9-16.
9. Baldwin, J.E.; Bradley, M. Chem. Rev. 1990, 90, 1079-1088.
10. (a) Ratcliffe, R.W.; Christensen, B.G. Tetrahedron Lett. 1973, 4645-4648.
11. (b) Ratcliffe, R.W.; Christensen, B.G. Tetrahedron Lett. 1973, 4649-4652.
12. (c) Christensen, B.G.; Ratcliffe, R.W. (Merck & Co. Inc.), DT 2 318 829, 1973.
13. (a) Staudinger, H. Justus Liebig's Ann. Chem. 1907, 356, 51-123.
14. (b) Bose, A.K.; Anjaneyulu, B. Chem. Ind. (London) 1966, 903-904.
15. Graymore, J. J. Chem. Soc. 1932, 1353-1357.
16. Ferrari, M.; Jommi, G.; Miglierini, G.; Pagliarin, R.; Sisti, M. Synth. Commun. 1992, 22, 107-123.
17. Preparation according to Stowell, J.C.; Ham, B.M.; Esslinger, M.A.; Duplantier, A.J. J. Org. Chem. 1989, 54, 1212-1213. Isolation according to Hartman, G.D.; Weinstock, L.M. Org. Synth. 1979, 59, 183-190.
18. Preparation according to Stowell, J.C.; Ham, B.M.; Esslinger, M.A.; Duplantier, A.J. J. Org. Chem. 1989, 54, 1212-1213. Isolation according to Hartman, G.D.; Weinstock, L.M. Org. Synth. 1979, 59, 183-190.
19. 2, 1/2 → 1/4, visualization on TLC with o-dianisidine/HOAc) to remove unchanged dichloroacetone and diacetoxyacetone.
20. (a) Boyer, J.H.; Hamer, J. J. Am. Chem. Soc. 1955, 77, 951-954.
21. (b) Bertho, A.; Maier, J. Justus Liebigs Ann. Chem. 1932, 498, 50-61.
22. (c) CAUTION! Azidoacetyl chloride was reported to decompose with explosive violence when treated inappropriately: Georg, G.I.; Ravikumar, V.T. in The Organic Chemistry of β-Lactams (Ed. G.I. Georg), VCH Publishers, New York, 1993, pp. 295-368; it is strongly recommended to prepare azidoacetyl chloride in small batches and to use a safety shield during its distillation.
23. Mobashery, S.; Johnston, M. J. Org. Chem. 1986, 51, 4723-4726.
24. Jeffrey, P.D.; McCombie, S.W. J. Org. Chem. 1982, 47, 587-590.
25. Firestone, R.A.; Maciejewicz, N.S.; Ratcliffe, R.W.; Christensen, B.G. J. Org. Chem. 1974, 39, 437-440.
26. Watanabe, T.; Sugawara, S.; Miyadera, T. Chem. Pharm. Bull. 1982, 30, 2579-2582.
27. (6R, 7S)-3-Acetoxymethyl-7-amino-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2- carboxylic acid was synthesized from natural (+)-7-ACA 1 according to Doherty, J.B.; et. al. J. Med. Chem. 1990, 33, 2513-2521 and kindly provided to us by Biochemie, Kundl.
28. Tschaen, D.M.; Fuentes, L.M.; Lynch, J.E.; Laswell, W.L.; Volante, R.P.; Shinkai, I. Tetrahedron Lett. 1988, 29, 2779-2782.
29. Shinbo, T.; Yamaguchi, T.; Nishimura, K.; Sugiura, M. J. Chrom. 1987, 405, 145-153.