Synthesis and some transformations of 1-azido-glycopyranosyl cyanides - Precursors of anomeric α-amino acids

Tetrahedron

Volumn 52, Issue 27, 1996, Pages 9121-9136

  Somsák, László ^a   Sós, Erzsébet ^a   Györgydeák, Zoltán ^a   Praly, Jean Pierre ^b   Descotes, Gérard ^b  

^a UNIVERSITY OF DEBRECEN   (Hungary)

^b UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID SYNTHESIS; ARTICLE; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030183218     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00440-1     Document Type: Article

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68. 24. Kewley, R. Can. J. Chem., 1974, 52, 509-516; Krol, M. C.; Huige, C. J. M.; Altona, C. J. Comput. Chem., 1990, 11, 765-790; Fernández, B.; Vázquez, S. A.; Ríos, M. A. J. Comput. Chem., 1992, 13, 722-729; Lichtenthaler, F. W.; Hoyer, F. Carbohydr. Res., 1994, 253, 141-150; compare also: KoD, P.; Fortsch, A. Carbohydr. Res., 1987, 171, 301-315.
69. 24. Kewley, R. Can. J. Chem., 1974, 52, 509-516; Krol, M. C.; Huige, C. J. M.; Altona, C. J. Comput. Chem., 1990, 11, 765-790; Fernández, B.; Vázquez, S. A.; Ríos, M. A. J. Comput. Chem., 1992, 13, 722-729; Lichtenthaler, F. W.; Hoyer, F. Carbohydr. Res., 1994, 253, 141-150; compare also: KoD, P.; Fortsch, A. Carbohydr. Res., 1987, 171, 301-315.
70. 24. Kewley, R. Can. J. Chem., 1974, 52, 509-516; Krol, M. C.; Huige, C. J. M.; Altona, C. J. Comput. Chem., 1990, 11, 765-790; Fernández, B.; Vázquez, S. A.; Ríos, M. A. J. Comput. Chem., 1992, 13, 722-729; Lichtenthaler, F. W.; Hoyer, F. Carbohydr. Res., 1994, 253, 141-150; compare also: KoD, P.; Fortsch, A. Carbohydr. Res., 1987, 171, 301-315.
71. 25. Kiss, L; Somsak, L. Carbohydr. Res., accepted for publication.
72. 26. Synthesis of (+)-hydantocidin a) from a 1-bromo-ribofuranosyl formaniide derivative: Harrington, P. M.; Jung, M. E. Tetrahedron Lett., 1994, 35, 5145-5148;
73. b) from a 1-azido-ribofuranosyl formamide derivative: réf. 4a; cf also 4f.
74. 27. Thornber, C. W. Chem. Soc. Rev., 1979, 8, 563-580.
75. 28. Recent reviews on tetrazoles: Wittenberger, S. J. OPPI, 1994, 26, 499-531; Koldobskii, G. I.; Ostrovskii, Y. A. Russ. Chem. Rev., 1994, 63, 797-814; Meier, H. R.; Heimgartner, H. in Methoden der Organischen Chemie (Houben-Weyl), (Ed.: Schaumann, E.), Thieme, 1994, Vol. E8d, pp. 664-795; C-grycosyl tetrazoles: Mahmoud, S. H.; Somsák, L.; Farkas, I. Carbohydr. Res., 1994, 254, 91-104.
76. 28. Recent reviews on tetrazoles: Wittenberger, S. J. OPPI, 1994, 26, 499-531; Koldobskii, G. I.; Ostrovskii, Y. A. Russ. Chem. Rev., 1994, 63, 797-814; Meier, H. R.; Heimgartner, H. in Methoden der Organischen Chemie (Houben-Weyl), (Ed.: Schaumann, E.), Thieme, 1994, Vol. E8d, pp. 664-795; C-grycosyl tetrazoles: Mahmoud, S. H.; Somsák, L.; Farkas, I. Carbohydr. Res., 1994, 254, 91-104.
77. 28. Recent reviews on tetrazoles: Wittenberger, S. J. OPPI, 1994, 26, 499-531; Koldobskii, G. I.; Ostrovskii, Y. A. Russ. Chem. Rev., 1994, 63, 797-814; Meier, H. R.; Heimgartner, H. in Methoden der Organischen Chemie (Houben-Weyl), (Ed.: Schaumann, E.), Thieme, 1994, Vol. E8d, pp. 664-795; C-grycosyl tetrazoles: Mahmoud, S. H.; Somsák, L.; Farkas, I. Carbohydr. Res., 1994, 254, 91-104.
78. 28. Recent reviews on tetrazoles: Wittenberger, S. J. OPPI, 1994, 26, 499-531; Koldobskii, G. I.; Ostrovskii, Y. A. Russ. Chem. Rev., 1994, 63, 797-814; Meier, H. R.; Heimgartner, H. in Methoden der Organischen Chemie (Houben-Weyl), (Ed.: Schaumann, E.), Thieme, 1994, Vol. E8d, pp. 664-795; C-grycosyl tetrazoles: Mahmoud, S. H.; Somsák, L.; Farkas, I. Carbohydr. Res., 1994, 254, 91-104.
79. 29. Myers, R. W.; Lee, Y. C. Carbohydr. Res., 1984, 132, 61-82, and refs. therein.
80. 30. Durette, P. L.; Horton, D. Carbohydr. Res., 1971, 18, 389-401.
81. 31. Paulsen, H. ; Györgydeák, Z.; Friedmann, M. Chem. Ber., 1974, 107, 1590-1613.
82. 32. Durette, P. L.; Horton, D. Adv. Carbohydr. Chem. Biochem., 1971, 26, 49-125.
83. 33. Dinya, Z.; Somsák, L. in preparation.
84. 15 which can transfer electrons to the substrate 1-bromo-glycosyl cyanides thereby building up a chain reaction. At the moment also the question "why do both anomers appear in the reaction of the D-xylo configurated substrates only" remains open. In order to understand these processes more deeply further investigations will have to be performed.