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Abstract:

From the reaction of octa-O-benzoyl-lactose (1) with methanolic ammonia, lactose, 1,1-bis(benzamido)-1-deoxy-4-O-β-D-galactopyranosyl-D-glucitol (2), and N-benzoyl-4-O-β-D-galactopyranosyl-D-glucopyranosylamine (3) were obtained. The behavior of some other octabenzoylated disaccharides in the ammonolysis reaction is discussed. © 1973.

Registro:

Documento: Artículo
Título:The reaction of ammonia with acylated disaccharides. Part X. Octa-O-benzoyl-lactose and other benzoyl derivatives of lactose
Autor:Deferrari, J.O.; Thiel, I.M.E.; 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
Palabras clave:ammonia; benzoic acid derivative; disaccharide; lactose; methanol; periodic acid; sugar alcohol; article; chemistry; oxidation reduction reaction; paper chromatography; synthesis; technique; Ammonia; Benzoates; Chemistry; Chromatography, Paper; Disaccharides; Lactose; Methanol; Methods; Oxidation-Reduction; Periodic Acid; Sugar Alcohols
Año:1973
Volumen:29
Número:1
Página de inicio:141
Página de fin:146
DOI: http://dx.doi.org/10.1016/S0008-6215(00)82077-7
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:ammonia, 14798-03-9, 51847-23-5, 7664-41-7; lactose, 10039-26-6, 16984-38-6, 63-42-3, 64044-51-5; methanol, 67-56-1; periodic acid, 10450-60-9, 13444-71-8; Ammonia, 7664-41-7; Benzoates; Disaccharides; Lactose, 63-42-3; Methanol, 67-56-1; Periodic Acid, 10450-60-9; Sugar Alcohols
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v29_n1_p141_Deferrari

Referencias:

  • Ness, Fletcher, Jr., (1952) J. Amer. Chem. Soc., 74, p. 5344
  • Deferrari, Thiel, Cadenas, The Reaction of Ammonia with Acylated Disaccharides. VI. Octa-O-benzoylcellobiose and Benzoyl Derivatives of Cellobiose (1965) The Journal of Organic Chemistry, 30, p. 3053
  • Thiel, Deferrari, Cadenas, (1966) J. Org. Chem., 31, p. 3704
  • Thiel, Deferrari, Cadenas, (1969) Ann., 723, p. 192
  • Vazquez, Deferrari, Thiel, (1973) Carbohyd. Res., 26, p. 351
  • Gros, Ondetti, Sproviero, Deulofeu, Deferrari, (1962) J. Org. Chem., 27, p. 924
  • Gros, Deulofeu, (1964) J. Org. Chem., 29, p. 3647
  • Zanlungo, Deferrari, Cadenas, Acyl migrations in acylated monosaccharides. Formation of N-acetyl-β-D-galactofuranosylamine (1969) Carbohydrate Research, 10, p. 403
  • Cadenas, Deferrari, (1961) Analyst, 86, p. 132
  • Partridge, (1949) Nature, 164, p. 443
  • Deferrari, Thiel, Cadenas, (1973) Carbohyd. Res., 26, p. 244
  • Hudson, Yanowsky, (1917) J. Amer. Chem. Soc., 39, p. 1013
  • Guthrie, (1962) Methods Carbohyd. Chem., 1, p. 440
  • Speck, Jr., (1962) Methods Carbohyd. Chem., 1, p. 443

Citas:

---------- APA ----------
Deferrari, J.O., Thiel, I.M.E. & Cadenas, R.A. (1973) . The reaction of ammonia with acylated disaccharides. Part X. Octa-O-benzoyl-lactose and other benzoyl derivatives of lactose. Carbohydrate Research, 29(1), 141-146.
http://dx.doi.org/10.1016/S0008-6215(00)82077-7
---------- CHICAGO ----------
Deferrari, J.O., Thiel, I.M.E., Cadenas, R.A. "The reaction of ammonia with acylated disaccharides. Part X. Octa-O-benzoyl-lactose and other benzoyl derivatives of lactose" . Carbohydrate Research 29, no. 1 (1973) : 141-146.
http://dx.doi.org/10.1016/S0008-6215(00)82077-7
---------- MLA ----------
Deferrari, J.O., Thiel, I.M.E., Cadenas, R.A. "The reaction of ammonia with acylated disaccharides. Part X. Octa-O-benzoyl-lactose and other benzoyl derivatives of lactose" . Carbohydrate Research, vol. 29, no. 1, 1973, pp. 141-146.
http://dx.doi.org/10.1016/S0008-6215(00)82077-7
---------- VANCOUVER ----------
Deferrari, J.O., Thiel, I.M.E., Cadenas, R.A. The reaction of ammonia with acylated disaccharides. Part X. Octa-O-benzoyl-lactose and other benzoyl derivatives of lactose. Carbohydr. Res. 1973;29(1):141-146.
http://dx.doi.org/10.1016/S0008-6215(00)82077-7