An efficient synthesis of N-protected threo (2R,3S)-3-amino-1,2-epoxy phenylbutane

Parkes, 1994, J. Org. Chem., 59, 3656, 10.1021/jo00092a026 Kaldor, 1997, J. Med. Chem., 40, 3979, 10.1021/jm9704098 Tung, R. D.; Hale. M. R.; Baker, C. T.; Furfine, E. S.; Kaldor, I.; Kazmierski, W. W.; Spaltenstein, A.R. Vertex Pharmaceuticals; U.S. Patent 6 559 137, 2003. Xu, 2002, Org. Proc. Res. Dev., 6, 323, 10.1021/op025504r Reetz, 1989, Tetrahedron Lett., 30, 5425, 10.1016/S0040-4039(01)80584-0 Ng, 1995, Tetrahedron, 51, 6397, 10.1016/0040-4020(95)00309-V Beaulieu, 1996, J. Org. Chem., 61, 3635, 10.1021/jo960109i Ng, J. S.; Przybyla, C. A.; Mueller, R. A.; Vazquez, M. L.; Getman, D. P.; G.D. Searle and Co., USA; Monsanto Co.; PCT Int. Appl., WO 9323388, 1993. Luly, 1987, J. Org. Chem., 52, 1487, 10.1021/jo00384a020 Sham, 1993, J. Chem. Soc., Chem. Commun., 1052, 10.1039/c39930001052 Malik, A. A.; Clement, T. E.; Palandoken, H.; Robinson, J.; Stringer, J. A.; Aerojet Fine Chemicals LLC; Eur. Pat. Appl., EP1050532, 2000. Onishi, 2001, Tetrahedron Lett., 42, 5887, 10.1016/S0040-4039(01)01115-7 Honda, 2002, Org. Lett., 4, 447, 10.1021/ol017163s Honda, 2004, Org. Biomol. Chem., 2, 2061, 10.1039/b404071f Suzuki, T.; Honda, Y.; Izawa, K.; Williams, R. M. J. Org. Chem. 2005, 70, in press. Suzuki, T.; Honda, Y.; Izawa, K.; Ajinomoto Co., Inc.; U.S. Patent 6 169 200, 2001. Suzuki, T.; Honda, Y.; Izawa, K.; Ajinomoto Co., Inc.; Eur. Pat. Appl., EP767168, 1997. Awaji, H.; Kaneka Corp.; Japan Kokai Tokyo Koho, JP08259519, 1996. Suzuki, T.; Honda, Y.; Izawa, K.; Ajinomoto Co., Inc.; Japan Kokai Tokkyo Koho, JP9323960, 1997. Braanalt, 1997, Tetrahedron Lett., 38, 3483, 10.1016/S0040-4039(97)00662-X Aguilar, 1998, J. Org. Chem., 63, 3560, 10.1021/jo9720851 Bennett, 1993, J. Chem. Soc., Chem. Commun., 737, 10.1039/C39930000737 Kang, 1995, Bioorg. Med. Chem. Lett., 5, 2959, 10.1016/0960-894X(95)00515-4 Aguilar, 1999, Tetrahedron Lett., 40, 3913, 10.1016/S0040-4039(99)00568-7 Russell, 1973, J. Am. Chem. Soc., 95, 4025, 10.1021/ja00793a032 Robins, 1976, J. Am. Chem. Soc., 98, 8213, 10.1021/ja00441a054 Norman, 1983, Synthesis, 304, 10.1055/s-1983-30313 Liu, 1985, Carbohydr. Res., 136, 273, 10.1016/0008-6215(85)85203-4 Kempf, D. J.; Norbeck, D. W.; Sham, H. L.; Zhao, C.; Sowin, T. J.; Reno, D. S.; Haight, A. R.; Abbott Laboratories; U.S. Patent 6 667 404, 2003. Ghosh, 1997, J. Org. Chem., 62, 6080, 10.1021/jo9706943 Honda, Y.; Arai, M.; Kaida, M.; Iwagami, H.; Ajinomoto, Co., Inc.; Japan Kokai Tokkyo Koho, JP01224390, 1989 Shiragami, 1996, Nucleosides Nucleotides, 15, 47, 10.1080/07328319608002369