A novel donor for the synthesis of 2-deoxy-β-glycosides

Chemical Communications

Volumn , Issue 23, 1996, Pages 2651-2652

  Marzabadi, Cecilia H ^a   Franck, Richard W ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002440090     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/CC9960002651     Document Type: Article

References (36)

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26. G. Capozzi, R. W. Franck, S. Menichetti, M. Mattioli, C. Nativi and G. Valle, J. Org. Chem., 1995, 60, 6416; G. Capozzi, A. Dios, R. W. Franck, A. Geer, C. Marzabadi, S. Menichetti, C. Nativi and M. Tamarez, Angew. Chem., Int. Ed. Engl., 1996, 35, 777.
27. A. T. Watson, K. Park, D. F. Wiemer and W. J. Scott, J. Org. Chem., 1995, 60, 5102 and ref. 17 therein. The methylene Wittig reagent also afforded the desired product, but in lower yield.
28. V. Bolitt, C. Mioskowski, S.-G. Lee and J. R. Falck, J. Org. Chem., 1990, 55, 5812; N. Kaila, M. Blumenstein, H. Bielawska and R. W. Franck, J. Org. Chem., 1992, 57, 2084; R. W. Franck, N. Kaila, M. Blumenstein, A. Geer, X. L. Huang and J. J. Dannenberg, J. Org. Chem., 1993, 58, 5335.
29. V. Bolitt, C. Mioskowski, S.-G. Lee and J. R. Falck, J. Org. Chem., 1990, 55, 5812; N. Kaila, M. Blumenstein, H. Bielawska and R. W. Franck, J. Org. Chem., 1992, 57, 2084; R. W. Franck, N. Kaila, M. Blumenstein, A. Geer, X. L. Huang and J. J. Dannenberg, J. Org. Chem., 1993, 58, 5335.
30. V. Bolitt, C. Mioskowski, S.-G. Lee and J. R. Falck, J. Org. Chem., 1990, 55, 5812; N. Kaila, M. Blumenstein, H. Bielawska and R. W. Franck, J. Org. Chem., 1992, 57, 2084; R. W. Franck, N. Kaila, M. Blumenstein, A. Geer, X. L. Huang and J. J. Dannenberg, J. Org. Chem., 1993, 58, 5335.
31. J. R. Marino-Albernas, R. Bittman, A. Peters and E. Mayhew, J. Med. Chem., 1996, 39, 3241.
32. For comparison with examples of conceptually similar sequences which employ arene sulfenyl electrophiles as reagents for activation of glycals followed by desulfurization, see N. Kaila and R. W. Franck, Carbohydr. Res., 1993, 239; W. R. Roush, K. Briner, B. S. Kesler, M. Murphy and D. J. Gustin, J. Org. Chem., 1996, 61, 6098; ref. 5. It can be seen that the sulfenyl activation involves the typical precautions required of very electrophilic species, that the processes are marginally less stereo-selective and that the desulfurization yields are also variable.
33. For comparison with examples of conceptually similar sequences which employ arene sulfenyl electrophiles as reagents for activation of glycals followed by desulfurization, see N. Kaila and R. W. Franck, Carbohydr. Res., 1993, 239; W. R. Roush, K. Briner, B. S. Kesler, M. Murphy and D. J. Gustin, J. Org. Chem., 1996, 61, 6098; ref. 5. It can be seen that the sulfenyl activation involves the typical precautions required of very electrophilic species, that the processes are marginally less stereo-selective and that the desulfurization yields are also variable.
34. For capsule reviews of 'latent/active' and 'disarmed/armed', see P. Collins and R. Ferrier, Monosaccharides, Their Chemistry and Their Role in Natural Products, Wiley, Chichester, 1995, p. 84; G.-J. Boons, Tetrahedron, 1996, 52, 1095: For a recent example, see ref. 8(b).
35. For capsule reviews of 'latent/active' and 'disarmed/armed', see P. Collins and R. Ferrier, Monosaccharides, Their Chemistry and Their Role in Natural Products, Wiley, Chichester, 1995, p. 84; G.-J. Boons, Tetrahedron, 1996, 52, 1095: For a recent example, see ref. 8(b).
36. Aspects of this work have been presented at the American Chemical Society meeting, New Orleans, March, 1996, ORGN#300 and the MARM of the American Chemical Society, Villanova, May 1996, no. 52.