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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 17, 1987 - Issue 9
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Original Articles

Practical Synthesis of (3R,4R)-4-Acetoxy-3-[1(R)-t-Butyldimethylsilyloxyethyl]Aze-Tidin-2-One. A Key Intermediate for Penem and Carbapenem Synthesis

Pages 1029-1033 | Published online: 19 Dec 2006

References

  • Yoshida , A. , Hayashi , T. , Takeda , N. , Oida , S. and Ohki , E. 1981 . Chem. Pharm. Bull. , 29 : 2899
  • Fujimoto , K. , Iwano , Y. and Hirai , K. 1985 . Tetrahedron Lett. , 26 : 89 Leanza, W.J., DiNinno, F., Muthard, D.A., Wilkening, R.R., Wildonger, K.J., Ratcliffe, R.W., and Christensen, B.G., Tetrahedron, 1983, 39, 2505; Ueda, Y., Roberge, G., and Vinet, V., Can. J. Chem., 1984, 62, 2936; Nagao, Y., Kumagai, T., Tamai, S., Abe, T., Kuramoto, Y., Taga, T., Aoyagi, S., Nagase, Y., Ochiai, M., Inoue, Y., and Fujita, E., J. Am. Chem. Soc., 1986, 108, 4673.
  • References cited in the publications of reference 2.
  • Martel , A. and Daris , J. P. 1986 . 596 : 677 US patent, US 4
  • Column: Porasil (Waters), Solvent: 3% CH3CN/CH2Cl Detection: uv 275 nm, Attenuation: 0.2
  • 1H-NMR (60MHz, CDC13): δ: 0.03 (s, 6H, CH3-Si), 0.83 (s, 9H, CH3-C-Si), 1.23 (d, J=6 Hz, 3H, CH3-CH-O), 1.93, 2.22 (2s, 6H, =C(CH3)2), 3.32 (dd, J=1.5 Hz, 1H, H-3), 3.71 (s, 3H, CO3CH3), 4.18 (m, 1H, CH3CHO), 5.86 (d, J=1.5 Hz, 1H, H-4)

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