Synthesis and radical fragmentation of carbohydrate anomeric nitrates. Formation of convenient chiral synthetic intermediates

Tetrahedron Asymmetry

Volumn 9, Issue 17, 1998, Pages 2975-2978

  Francisco, Cosme G ^a   León, Elisa I ^a   Moreno, Pilar ^a   Suárez, Ernesto ^a  

^a INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALDITOL; NITRIC ACID DERIVATIVE;

ARTICLE; CARBOHYDRATE ANALYSIS; CHIRALITY; DRUG SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0344936077     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00326-7     Document Type: Article

References (43)

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32. Abushanab, E.; Vemishetti, P.; Leiby, R. W.; Singh, H. K.; Mikkilineni, A. B.; Wu, D. C.-J.; Saibaba, R.; Panzica, R. P. J. Org. Chem. 1988, 53, 2598-2602. Le Merre, Y.; Gravier-Pelletier, C.; Dumas, J.; Depezay, J. C. Tetrahedron Lett. 1990, 31, 1003-1006. Pottie, M.; Van der Eycken, J.; Röper, H.; Vandewalle, M. Tetrahedron: Asymmetry 1991, 2, 329-330. Pottie, M.; De Lathauwer, G.; Vandewalle, M. Bull. Soc. Chim. Belg. 1994, 103, 285-294. Flasche, M.; Scharf, H.-D. Tetrahedron: Asymmetry 1995, 6, 1543-1546.
33. Abushanab, E.; Vemishetti, P.; Leiby, R. W.; Singh, H. K.; Mikkilineni, A. B.; Wu, D. C.-J.; Saibaba, R.; Panzica, R. P. J. Org. Chem. 1988, 53, 2598-2602. Le Merre, Y.; Gravier-Pelletier, C.; Dumas, J.; Depezay, J. C. Tetrahedron Lett. 1990, 31, 1003-1006. Pottie, M.; Van der Eycken, J.; Röper, H.; Vandewalle, M. Tetrahedron: Asymmetry 1991, 2, 329-330. Pottie, M.; De Lathauwer, G.; Vandewalle, M. Bull. Soc. Chim. Belg. 1994, 103, 285-294. Flasche, M.; Scharf, H.-D. Tetrahedron: Asymmetry 1995, 6, 1543-1546.
34. Abushanab, E.; Vemishetti, P.; Leiby, R. W.; Singh, H. K.; Mikkilineni, A. B.; Wu, D. C.-J.; Saibaba, R.; Panzica, R. P. J. Org. Chem. 1988, 53, 2598-2602. Le Merre, Y.; Gravier-Pelletier, C.; Dumas, J.; Depezay, J. C. Tetrahedron Lett. 1990, 31, 1003-1006. Pottie, M.; Van der Eycken, J.; Röper, H.; Vandewalle, M. Tetrahedron: Asymmetry 1991, 2, 329-330. Pottie, M.; De Lathauwer, G.; Vandewalle, M. Bull. Soc. Chim. Belg. 1994, 103, 285-294. Flasche, M.; Scharf, H.-D. Tetrahedron: Asymmetry 1995, 6, 1543-1546.
35. 2.
36. Taunton, J. Collins, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1996, 118, 10412-10422. Abushanab, E.; Bessodes, M.; Antonakis, K. Tetrahedron Lett. 1984, 25, 3841-3844. Pierce, M. E.; Harris, G. D.; Islam, Q.; Radesca, L. A.; Storace, L.; Waltermire, R. E.; Wat, E.; Jadhav, P. K.; Emmett, G. C. J. Org. Chem. 1996, 61, 444-450. Metz, P.; Schoop, A. Tetrahedron 1993, 49, 10597-10608. Somfai, P. J. Chem. Soc., Perkin Trans. 1 1995, 817-819. Somfai, P. Tetrahedron 1994, 50, 11315-11320. Kang, S. H.; Choi, H. J. Chem. Soc., Chem. Commun. 1996, 1521-1522. Hanessian, S.; Gauthier, J.-Y.; Okamoto, K.; Beauchamp, A. L.; Theophanides, T. Can. J. Chem. 1993, 71, 880-885.
37. Taunton, J. Collins, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1996, 118, 10412-10422. Abushanab, E.; Bessodes, M.; Antonakis, K. Tetrahedron Lett. 1984, 25, 3841-3844. Pierce, M. E.; Harris, G. D.; Islam, Q.; Radesca, L. A.; Storace, L.; Waltermire, R. E.; Wat, E.; Jadhav, P. K.; Emmett, G. C. J. Org. Chem. 1996, 61, 444-450. Metz, P.; Schoop, A. Tetrahedron 1993, 49, 10597-10608. Somfai, P. J. Chem. Soc., Perkin Trans. 1 1995, 817-819. Somfai, P. Tetrahedron 1994, 50, 11315-11320. Kang, S. H.; Choi, H. J. Chem. Soc., Chem. Commun. 1996, 1521-1522. Hanessian, S.; Gauthier, J.-Y.; Okamoto, K.; Beauchamp, A. L.; Theophanides, T. Can. J. Chem. 1993, 71, 880-885.
38. Taunton, J. Collins, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1996, 118, 10412-10422. Abushanab, E.; Bessodes, M.; Antonakis, K. Tetrahedron Lett. 1984, 25, 3841-3844. Pierce, M. E.; Harris, G. D.; Islam, Q.; Radesca, L. A.; Storace, L.; Waltermire, R. E.; Wat, E.; Jadhav, P. K.; Emmett, G. C. J. Org. Chem. 1996, 61, 444-450. Metz, P.; Schoop, A. Tetrahedron 1993, 49, 10597-10608. Somfai, P. J. Chem. Soc., Perkin Trans. 1 1995, 817-819. Somfai, P. Tetrahedron 1994, 50, 11315-11320. Kang, S. H.; Choi, H. J. Chem. Soc., Chem. Commun. 1996, 1521-1522. Hanessian, S.; Gauthier, J.-Y.; Okamoto, K.; Beauchamp, A. L.; Theophanides, T. Can. J. Chem. 1993, 71, 880-885.
39. Taunton, J. Collins, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1996, 118, 10412-10422. Abushanab, E.; Bessodes, M.; Antonakis, K. Tetrahedron Lett. 1984, 25, 3841-3844. Pierce, M. E.; Harris, G. D.; Islam, Q.; Radesca, L. A.; Storace, L.; Waltermire, R. E.; Wat, E.; Jadhav, P. K.; Emmett, G. C. J. Org. Chem. 1996, 61, 444-450. Metz, P.; Schoop, A. Tetrahedron 1993, 49, 10597-10608. Somfai, P. J. Chem. Soc., Perkin Trans. 1 1995, 817-819. Somfai, P. Tetrahedron 1994, 50, 11315-11320. Kang, S. H.; Choi, H. J. Chem. Soc., Chem. Commun. 1996, 1521-1522. Hanessian, S.; Gauthier, J.-Y.; Okamoto, K.; Beauchamp, A. L.; Theophanides, T. Can. J. Chem. 1993, 71, 880-885.
40. Taunton, J. Collins, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1996, 118, 10412-10422. Abushanab, E.; Bessodes, M.; Antonakis, K. Tetrahedron Lett. 1984, 25, 3841-3844. Pierce, M. E.; Harris, G. D.; Islam, Q.; Radesca, L. A.; Storace, L.; Waltermire, R. E.; Wat, E.; Jadhav, P. K.; Emmett, G. C. J. Org. Chem. 1996, 61, 444-450. Metz, P.; Schoop, A. Tetrahedron 1993, 49, 10597-10608. Somfai, P. J. Chem. Soc., Perkin Trans. 1 1995, 817-819. Somfai, P. Tetrahedron 1994, 50, 11315-11320. Kang, S. H.; Choi, H. J. Chem. Soc., Chem. Commun. 1996, 1521-1522. Hanessian, S.; Gauthier, J.-Y.; Okamoto, K.; Beauchamp, A. L.; Theophanides, T. Can. J. Chem. 1993, 71, 880-885.
41. Taunton, J. Collins, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1996, 118, 10412-10422. Abushanab, E.; Bessodes, M.; Antonakis, K. Tetrahedron Lett. 1984, 25, 3841-3844. Pierce, M. E.; Harris, G. D.; Islam, Q.; Radesca, L. A.; Storace, L.; Waltermire, R. E.; Wat, E.; Jadhav, P. K.; Emmett, G. C. J. Org. Chem. 1996, 61, 444-450. Metz, P.; Schoop, A. Tetrahedron 1993, 49, 10597-10608. Somfai, P. J. Chem. Soc., Perkin Trans. 1 1995, 817-819. Somfai, P. Tetrahedron 1994, 50, 11315-11320. Kang, S. H.; Choi, H. J. Chem. Soc., Chem. Commun. 1996, 1521-1522. Hanessian, S.; Gauthier, J.-Y.; Okamoto, K.; Beauchamp, A. L.; Theophanides, T. Can. J. Chem. 1993, 71, 880-885.
42. Taunton, J. Collins, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1996, 118, 10412-10422. Abushanab, E.; Bessodes, M.; Antonakis, K. Tetrahedron Lett. 1984, 25, 3841-3844. Pierce, M. E.; Harris, G. D.; Islam, Q.; Radesca, L. A.; Storace, L.; Waltermire, R. E.; Wat, E.; Jadhav, P. K.; Emmett, G. C. J. Org. Chem. 1996, 61, 444-450. Metz, P.; Schoop, A. Tetrahedron 1993, 49, 10597-10608. Somfai, P. J. Chem. Soc., Perkin Trans. 1 1995, 817-819. Somfai, P. Tetrahedron 1994, 50, 11315-11320. Kang, S. H.; Choi, H. J. Chem. Soc., Chem. Commun. 1996, 1521-1522. Hanessian, S.; Gauthier, J.-Y.; Okamoto, K.; Beauchamp, A. L.; Theophanides, T. Can. J. Chem. 1993, 71, 880-885.
43. Taunton, J. Collins, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1996, 118, 10412-10422. Abushanab, E.; Bessodes, M.; Antonakis, K. Tetrahedron Lett. 1984, 25, 3841-3844. Pierce, M. E.; Harris, G. D.; Islam, Q.; Radesca, L. A.; Storace, L.; Waltermire, R. E.; Wat, E.; Jadhav, P. K.; Emmett, G. C. J. Org. Chem. 1996, 61, 444-450. Metz, P.; Schoop, A. Tetrahedron 1993, 49, 10597-10608. Somfai, P. J. Chem. Soc., Perkin Trans. 1 1995, 817-819. Somfai, P. Tetrahedron 1994, 50, 11315-11320. Kang, S. H.; Choi, H. J. Chem. Soc., Chem. Commun. 1996, 1521-1522. Hanessian, S.; Gauthier, J.-Y.; Okamoto, K.; Beauchamp, A. L.; Theophanides, T. Can. J. Chem. 1993, 71, 880-885.