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Abstract:

Penta-O-nicotinoyl-α-D-glucopyranose reacts with aqueous ammonia to yield N-nicotinoyl-D-glucofuranosylamine, 1-deoxy-1,1-bis(nicotinamido)-D-glucitol, and 2-(D-arabino-tetrahydroxybutyl)-6-(D-erythro-2,3,4-trihydroxybutyl)pyrazine. The structure of these compounds was ascertained by use of oxidation techniques and spectroscopic data. The formation of the pyrazine compound is discussed. © 1972.

Registro:

Documento: Artículo
Título:The reaction of penta-O-nicotinoyl-α-D-glucopyranose with aqueous ammonia
Autor:Forlano, E.A.; Deferrari, J.O.; Cadenas, R.A.
Filiación:Departamento de Quimica Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Argentina
Departamento de Quimica, Facultad de agronomia y Veterinaria, Universidad de Buenos Aires, Argentina
Año:1972
Volumen:23
Número:1
Página de inicio:111
Página de fin:119
DOI: http://dx.doi.org/10.1016/S0008-6215(00)81582-7
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v23_n1_p111_Forlano

Referencias:

  • Forlano, Deferrari, Cadenas, (1972) Carbohyd. Res., 21, p. 484
  • Zanlungo, Deferrari, Cadenas, (1970) Carbohyd. Res., 14, p. 245
  • Mason, 246. The electronic spectra of N-heteroaromatic systems. Part II. Substituted monocyclic azones (1959) Journal of the Chemical Society (Resumed), p. 1247
  • Kuhn, Krüger, Haas, Seeliger, (1961) Ann., 644, p. 117
  • Fujii, Kikuchi, Kushida, (1966) J. Org. Chem., 31, p. 2239
  • Mager, Berends, (1958) Rec. Trav. Chim., 77, p. 829
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  • Horton, Miller, (1965) J. Org. Chem., 30, p. 2457
  • Cantley, Hough, Pittet, (1959) Chem. Ind., p. 1126. , London
  • Cantley, Hough, Pittet, (1959) Chem. Ind., p. 1253. , London
  • Cantley, Hough, Pittet, 465. The non-malapradian oxidation of carbohydrates and related compounds by periodate (1963) Journal of the Chemical Society (Resumed), p. 2527
  • Jezo, Luzak, (1963) Chem. Zvesti, 17, p. 255
  • Deulofeu, Deferrari, (1952) J. Org. Chem., 17, p. 1087
  • Falkner, Harrison, 239. The kinetics of alkaline hydrolysis of 2-, 3-, and 4-ethoxycarbonylpyridines and their 1-oxides (1960) Journal of the Chemical Society (Resumed), p. 1171
  • Zanlungo, Deferrari, Cadenas, Acyl migrations in acylated monosaccharides. Formation of N-acetyl-β-D-galactofuranosylamine (1969) Carbohydrate Research, 10, p. 403
  • Cadenas, Defferrari, The Reaction of Ammonia with Acylated Disaccharides. III. Acetyl Derivatives of Maltose and an Interpretation (1963) The Journal of Organic Chemistry, 28, p. 2613
  • Cadenas, Defferrari, (1961) Analyst, 86, p. 132
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  • Fujii, Kushida, (1966) J. Org. Chem., 31, p. 2406
  • Gabriel, Sonn, Übergang von der Chinoxalin zur Pyrazinereihe (1907) Berichte der deutschen chemischen Gesellschaft, 40, p. 4850
  • Schut, Mager, Berends, Investigations on pyrazine derivatives. VII: On the conversion of pyrazine 2,5-dicarboxylic acid into some derivatives of 2-aminopyrazine 5-carboxylic acid (1961) Recueil des Travaux Chimiques des Pays-Bas, 80, p. 391

Citas:

---------- APA ----------
Forlano, E.A., Deferrari, J.O. & Cadenas, R.A. (1972) . The reaction of penta-O-nicotinoyl-α-D-glucopyranose with aqueous ammonia. Carbohydrate Research, 23(1), 111-119.
http://dx.doi.org/10.1016/S0008-6215(00)81582-7
---------- CHICAGO ----------
Forlano, E.A., Deferrari, J.O., Cadenas, R.A. "The reaction of penta-O-nicotinoyl-α-D-glucopyranose with aqueous ammonia" . Carbohydrate Research 23, no. 1 (1972) : 111-119.
http://dx.doi.org/10.1016/S0008-6215(00)81582-7
---------- MLA ----------
Forlano, E.A., Deferrari, J.O., Cadenas, R.A. "The reaction of penta-O-nicotinoyl-α-D-glucopyranose with aqueous ammonia" . Carbohydrate Research, vol. 23, no. 1, 1972, pp. 111-119.
http://dx.doi.org/10.1016/S0008-6215(00)81582-7
---------- VANCOUVER ----------
Forlano, E.A., Deferrari, J.O., Cadenas, R.A. The reaction of penta-O-nicotinoyl-α-D-glucopyranose with aqueous ammonia. Carbohydr. Res. 1972;23(1):111-119.
http://dx.doi.org/10.1016/S0008-6215(00)81582-7