Asymmetric synthesis of diethyl (R)-(í)-(1-amino-3-methylbutyl)phosphonate :[ Phosphonic acid, (1-amino-3-methylbutyl)-, diethyl ester, (R)-]

Organic Syntheses

Volumn 75, Issue , 1998, Pages 19-

  Smith, Amos B ^b   Yager, Kraig M ^b   Phillips, Barton W ^b   Taylor, Carol M ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85027856898     PISSN: 00786209     EISSN: 16000730     Source Type: Book Series    
DOI: 10.15227/orgsyn.075.0019     Document Type: Article

References (27)

1. Procedure adapted from: Meyers, A. I.; Poindexter, G. S.; Brich, Z. J. Org. Chem. 1978, 43, 892.
2. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543
3. For comprehensive reviews, Kafarski, P.; Lejczak, B. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 63, 193;
4. Bartlett, P. A.; Marlowe, C. K.; Giannousis, P. P.; Hanson, J. E. Cold Spring Harbor Symp. Quant. Biol. 1987, 52, 83;
5. Bird, J.; De Mello, R. C.; Harper, G. P.; Hunter, D. J.; Karran, E. H.; Markwell, R. E.; Miles-Williams, A. J.; Rahman, S. S.; Ward, R. W. J. Med. Chem. 1994, 37, 158;
6. McLeod, D. A.; Brinkworth, R. I.; Ashley, J. A.; Janda, K. D.; Wirsching, P. Bioorg. Med. Chem. Lett. 1991, 1, 653.
7. Allen, J. G.; Atherton, F. R.; Hall, M. J.; Hassall, C. H.; Holmes, S. W.; Lambert, R. W.; Nisbet, L. J.; Ringrose, P. S. Nature 1978, 272, 56;
8. Atherton, F. R.; Hall, M. J.; Hassall, C. H.; Lambert, R. W.; Ringrose, P. S. Antimicrob. Agents Chemother. 1979, 15, 677;
9. Allen, J. G.; Atherton, F. R.; Hall, M. J.; Hassall, C. H.; Holmes, S. W.; Lambert, R. W.; Nisbet, L. J.; Ringrose, P. S. Antimicrob. Agents Chemother. 1979, 15, 684;
10. Atherton, F. R.; Hall, M. J.; Hassall, C. H.; Lambert, R. W.; Lloyd, W. J.; Ringrose, P. S. Antimicrob. Agents Chemother. 1979, 15, 696.
11. Kase, H.; Yamato, M.; Koguchi, T.; Okachi, R.; Kasai, M.; Shirahata, K.; Kawamoto, I.; Shuto, K.; Karasawa, A., et al. Eur. Pat. Appl. EP 61,172;
12. Chem. Abstr. 1983, 98, 107793m.
13. Hirschmann, R.; Smith, A. B., III; Taylor, C. M.; Benkovic, P. A.; Taylor, S. D.; Yager, K. M.; Sprengeler, P. A.; Benkovic, S. J.; Science 1994, 265, 234.
14. Gilmore, W. F., McBride, H. A. J. Am. Chem. Soc. 1972, 94, 4361.
15. Dhawan, B.; Redmore, D. Phosphorus Sulfur 1987, 32, 119.
16. Yokomatsu, T.; Shibuya, S. Tetrahedron: Asymmetry 1992, 3, 377.
17. Jacquier, R.; Ouazzani, F.; Roumestant, M. L.; Viallefont, P. Phosphorus Sulfur 1988, 36, 73.
18. Ferrari, M.; Jommi, G.; Miglierini, G.; Pagliarin, R.; Sisti, M. Synth. Commun. 1992, 22, 107.
19. Hanessian, S.; Bennani, Y. L. Tetrahedron Lett. 1990, 31, 6465.
20. Yager, K. M.; Taylor, C. M.; Smith, A. B., III J. Am. Chem. Soc. 1994, 116, 9377.
21. Huber, R.; Knierzinger, A.; Obrecht, J.-P.; Vasella, A. Helv. Chim. Acta 1985, 68, 1730: (S)-(+)-Phosphovaline diethyl ester, [Į] D 25 +0.4° (CHCl3, c 1.7); (S)-(+)-phosphoalanine diethyl ester, [Į] D 25 +7.3° (CHCl3, c 1.3); (S)-(+)-phosphoserine diethyl ester, [Į] D 25 +9.0° (CHCl3, c 1.0).
22. (R)-(í)-Phospholeucine, mp 288-291°C; [Į] D 25 í28° (1 M NaOH, c 1): Lejczak, B.; Kafarski, P.; Mastalerz, P. J. Chromatogr. 1985, 324, 455;
23. this work: mp 281-283°C (dec); [Į] D 25 í24.7° (1 M NaOH, c 0.7). (S)-(í)-Phosphomethionine, [Į] D 25 í40.4° (0.25 M NaOH, c 1.0): Kupczk-Subotkowska, L.; Mastalerz, P. Int. J. Pepti. Protein Res. 1983, 21, 485;
24. this work: (R)-(+)Phosphomethionine, mp 248-251°C (dec); [Į] D 25 +39.1° (0.25 M NaOH, c 1.1). (R)-(í)-Phosphoglutamic acid, mp 183-184°C; [Į] D 25 í20° (1 M NaOH, c 1): Lejczak, B.; Kafarski, P.; Mastalerz, P. J. Chromatogr. 1985, 324, 455;
25. this work: mp 175-177°C; [Į] D 25 í7° (1 M NaOH, c 0.7). (R)-(í)-Phospho(phenylglycine), [Į] D 25 +18° (1 M NaOH, c 2): Glowiak, T.; Sawka-Dobrowolska, W.; Kowalik, J.; Mastalerz, P.; Soroka, M.; Zon J. Tetrahedron Lett. 1977, 3965; this work: mp 282-284°C (dec); [Į] D 25 +16.6° (1 M NaOH, c 0.42).
26. Shiao, M. J.; Yang, C.- Y.; Lee, S. H.; Wu, T. C. Synth. Commun. 1988, 18, 359.
27. For preparation of starting aldehyde Kolb, M.; Barth, J.; Heydt, J. G.; Jung, M. J. J. Med. Chem. 1987, 30, 267.