The effect of cesium fluoride-DMF in the dibutylstannylene acetal-mediated selective monobenzylation of methyl 2,3-D-glycerate

Acta Chemica Scandinavica

Volumn 52, Issue 6, 1998, Pages 819-823

  Arukwe, Joseph ^a  

^a NYCOMED IMAGING AS   (Norway)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0347005969     PISSN: 0904213X     EISSN: None     Source Type: Journal    
DOI: 10.3891/acta.chem.scand.52-0819     Document Type: Article

References (39)

1. (a) Evans, D. A., Kaldor, S. W., Jones, T. K., Clardy, J. and Stout, T. J. J. Am. Chem. Soc. 112 (1990) 7001;
2. (b) Nicolaou, K. C., Ueno, H., Liu, J.-J., Nantermet, P. G., Yang, Z., Renaud, J., Paulvannan, K. and Chadha, R. J. Am. Chem. Soc. 117 (1995) 653;
3. (c) Hudlicky, T., Seoane, G. and Pettus, T. J. Org. Chem. 54 (1989) 4239;
4. (d) Kozaki, S., Sakanaka., Yasuda, T., Shimazu, T., Ogawa, E. and Saumi. T. J. Org. Chem. 53 (1988) 281;
5. (e) Sharpless, K. B. and Fleming, P. R. J. Org. Chem. 56 (1991) 2869.
6. (a) McDougal, P. G., Rico, J. G., Oh, Y,-I. and Condo, B. D. J. Org. Chem. 51 (1988) 3388;
7. (b) De Ninno, M. P., Etienne, J. B. and Duplantier, K. C. Tetrahedron Lett. 36 (1995) 669;
8. (c) Nishiguchi, T., Fugisaki, S., Ishii, Y., Yano, Y. and Nishida, A. J. Org. Chem. 59 (1994) 1191.
9. (a) Leigh, D. A., Martin, R. P., Smart, J. P. and Truscello, A. M. J. Chem. Soc., Chem. Commun. (1994) 1373;
10. (b) Takaku, H., Kamaike, K. and Tsuchiya, H J. Org. Chem. 49 (1984) 51;
11. (c) Auge, C., David, S. M. and Veyrieres, A. J. Chem. Soc., Chem. Commun. (1976) 375.
12. Byun, H.-S., Kumar, E. R. and Bittman, R. J. Org. Chem. 59 (1994) 2630.
13. Boons, G.-J., Castle, G. H., Clase, J. A., Grice, P., Ley, S. V. and Pinel, C. Synlett (1993) 913.
14. (a) Herradon, B., Morcuende, A. and Valverde, S. Synlett (1995) 455;
15. (b) Herradon, B., Morcuende, A. and Valverde, S. Synlett (1994) 89.
16. (a) Guilbert, B., Davis, N. J. and Flitcsh, S. L. Tetrahedron Lett. 35 (1994) 6563;
17. (b) Dasgupta, F. and Garegg, P. J. Synthesis (1994) 1121;
18. (c) Hanessian, S. and Davis, S. Tetrahedron 41 (1985) 643;
19. (d) Qin, H. and Grindley, T. B. J. Carbohydr. Chem. 15 (1996) 95; Flasche, M. and Scharf, H.-D. Tetrahedron Asymmetry 6 (1995) 1543.
20. (d) Qin, H. and Grindley, T. B. J. Carbohydr. Chem. 15 (1996) 95; Flasche, M. and Scharf, H.-D. Tetrahedron Asymmetry 6 (1995) 1543.
21. Ohno, M. and Nagashima, N. Chem. Lett. (1987) 141.
22. Nagashima, N. and Ohno, M. Chem. Pharm. Bull. 39 (1991) 1972.
23. (a) Reid, E. E. Ind. Eng. Chem. 29 (1937) 1344;
24. (b) Sridharan, R. and Mathai, I. M. J. Sci. Ind. Res. (1974) 178.
25. Olah, G., Narang, S. C., Salem, G. F. and Gupte, B. G. B. Synthesis (1981) 142.
26. Luthowy, R. and Meneghini, F. J. Org. Chem. 38 (1973) 2405.
27. (a) Taschner, E. and Liberek, B. Rocz. Chem. 30 (1956) 323;
28. (b) Elsinger, F., Schreiber, J. and Eschenmoser, A. Helv. Chim. Acta 43 (1960) 113.
29. (a) Mendelson, W. L. and Hayden, S. Synth. Commun. 26 (1996) 603;
30. (b) Downie, I. M., Earle, M. J., Heaney, H. and Shuhaibar, K. Tetrahedron 49 (1993) 4015;
31. (c) Buehler, C. A. and Pearson, D. E. Survey of Organic Syntheses, Vol. 1 (1970) p. 860.
32. Jugie, G., Smith, A. S. and Martin, G.J. J. Chem. Soc., Perkin Trans. 2 (1975) 925.
33. Cooper, S. Acc. Chem. Res. 21 (1988) 141.
34. Johnson, A. P. and Pelter, A. J. Chem. Soc. (1964) 520.
35. Otera, J. Chem. Rev. 93 (1993) 1449.
36. (a) Groutas, W. C. and Felker, D. Synthesis (1980) 861;
37. (b) Ho, T.-L, and Olah, G. Synthesis (1977) 417;
38. (c) Jung, M. E. and Lyster, M. A. J. Am. Chem. Soc. 99 (1977) 968;
39. (d) Jung, M. E. and Lyster, M. A. J. Org. Chem. 42 (1977) 3761.