Synthesis of N1-unsubstituted (β-lactams : Introducing n1-(1'-thiophenyl)benzyl as an N-protecting group

Tetrahedron Letters

Volumn 38, Issue 24, 1997, Pages 4281-4284

  Karupaiyan, K ^a   Srirajan, V ^a   Deshmukh, A R A S ^a   Bhawal, B M ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030957855     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00879-4     Document Type: Article

References (33)

1. a) Morin, R. B.; Gorman, H.; Ed, "Chemistry and Biology of β-lactam antibiotics" Acadamic press, Vol. 1, New York, 1982.
2. b) Sammes, P.G.; Ed, "Topics in Antibiotic Chemistry" Vol. 3, Ellis Howood Ltd., 1980.
3. c) O'Sullivan, J.; Abraham, E.P.; "Antibiotics" Vol. IV Ed., Springer - Verlag : Berlin, 1981.
4. d) Recent progress in the Chemical synthesis of Antibiotics : Lukacs, G.; Ohno, M.; Eds.; Springer : Berlin, 1990.
5. e) Georg, G. I.; Ed, "Organic Chemistry of β-lactams" VCH, New York, 1993.
6. f) Ojima, I. Acc. Chem. Res. 1995, 28, 383.
7. a) Srirajan, V.; Deshmukh, A.R.A.S.; Puranik, V.G.; Bhawal, B.M. Tetrahedron Asymmetry, 1996, 7, 2733.
8. b) Srirajan, V.; Deshmukh, A.R.A.S.; Bhawal, B.M. Tetrahedron, 1996, 52, 5585.
9. c) Jayaraman, M.; Puranik, V.G.; Bhawal, B.M. Tetrahedron 1996, 52, 9005.
10. a) Reuschling, D.; Pietsch, H.; Linkies, A. Tetrahedron Lett. 1978, 618.
11. b) Evans, D.A.; Sjogren, E.B. Tetrahedron Lett. 1985, 26, 3783, 3787.
12. c) Thomas, R.C. Tetrahedron Lett. 1989, 30, 5239.
13. d) Aszodi, J.; Bonnet, A.; Teutsch, G. Tetrahedron 1990, 46, 1579.
14. d) Kishimoto, S.; Sendai, M.; Tomimoto, M.; Hashiguchi, S.; Matsuo, T.; Ochiai, M. Chem. Pharm. Bull. 1984, 32, 2646.
15. a) Georg, G.I.; Kant, J.; He, P.; Ly, A.M.; Lampe, L. Tetrahedron Lett. 1988, 29, 2409.
16. b) Georg, G.I.; He, P.; Kant, J.; Mudd, J. Tetrahedron Lett. 1990, 31, 1497.
17. c) Bhattrai, K.; Cainelli, G.; Panunzio, M. Synlett 1990, 229.
18. d) Yanagisawa, H.; Ando, A.; Shiozaki, M.; Hiraoka, T. Tetrahedron Lett. 1983, 24, 1037.
19. a) Iimori, T.; Takahashi, Y.; Izawa, T.; Kobayashi, S.; Ohno, M.J. J. Am. Chem. Soc. 1983, 105, 1659.
20. b) Kametani, T.; Nagahara, T.; Honda, T. J. Org. Chem. 1985, 50, 2327.
21. c) Dolle, R.E.; Hughes, M.J.; Li, C.-S.; Kruse, L.I. J. Chem. Soc. Chem. Common. 1989, 148.
22. d) Shibya, M.; Jinbo, Y.; Kubota, S. Chem. Pharm. Bull. 1984, 32, 1303.
23. e) Okano, K.; Kyotani, Y.; Ishihama, H.; Kobayashi, S.; Ohno, M. J. Am. Chem. Soc. 1983, 105, 7186.
24. f) Shibasaki, M.; Ishida, Y.; Okabe, N. Tetrahedron Lett. 1985, 26, 2217.
25. a) Kronenthal, D.R.; Han, C.Y.; Taylor, M.K. J. Org. Chem. 1982, 47, 2765.
26. b) Corley, E.G.; Karady, S.; Abramson, N.L.; Ellison, D.; Weinstock, L.M. Tetrahedron Lett. 1988, 29, 2409.
27. Kupfer, R.; Brinker, U.H. J. Org. Chem. 1996, 61, 4185 and references cited therein.
28. Dougherty, G.; Taylor, W.H. J. Am. Chem. Soc. 1933, 55, 4588.
29. 3,4 = 4-5 Hz) of the crude reaction mixture.
30. -1.
31. 2O) flow rate 1.5 mL/min.
32. For details see : Srirajan, V.; Bhawal, B.M; Puranik, V.G. Acta. Cryst. C (in press).
33. 2: C, 75.30; H, 5.48; N, 5.85. Found : C, 75.51; H, 5.73; N, 5.62.