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Abstract:

Octa-O-acetylmelibiononitrile (1) was prepared from melibiose oxime. The reaction of aqueous ammonia with 1 gave 1,1-bis(acetamido)-1-deoxy-5-O-α-D-galactopyranosyl-D-arabinitol (2), N-acetyl-5-O-α-D-galactopyranosyl-α-D-arabinofuranosylamine (3), and the anomeric pair of 5-O-α-D-galactopyranosyl-D-arabinofuranoses (4 and 5). The hepta-O-acetyl derivative of 2 was prepared, and the acyclic structure of the nitrogen-containing moiety was established by oxidation with periodate. The α anomeric configuration of 3 was demonstrated by periodate oxidation and subsequent reduction with sodium borohydride and hydrolysis. © 1973.

Registro:

Documento: Artículo
Título:The reaction of ammonia with acylated disaccharides. XI. The wohl reaction with octa-O-acytylmelibiononitrile
Autor:Deferrari, J.O.; Zuazo, B.N.; Gelpi, M.E.
Filiación:Departamento de Quimica Organica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón II, Ciudad Universitaria, Buenos Aires Argentina
Año:1973
Volumen:30
Número:2
Página de inicio:313
Página de fin:318
DOI: http://dx.doi.org/10.1016/S0008-6215(00)81817-0
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v30_n2_p313_Deferrari

Referencias:

  • Cerezo, Sproviero, Deulofeu, Delpy, (1968) Carbohyd. Res., 7, p. 395. , and references cited therein
  • Zanlungo, Deferrari, Cadenas, (1970) Carbohyd. Res., 14, p. 245. , and references cited therein
  • Deferrari, Gelpi, Cadenas, (1965) J. Org. Chem., 30, p. 2328
  • Deferrari, Gelpi, Cadenas, (1965) J. Org. Chem., 30, p. 4065
  • Zemplén, Abbau der reduzierenden Biosen, V.: Konstitutions-Ermittlung der Melibiose und der Raffinose (1927) Berichte der deutschen chemischen Gesellschaft (A and B Series), 60, p. 923
  • Cerezo, Deulofeu, (1966) Carbohyd. Res., 2, p. 35
  • Tate, Bishop, THIN LAYER CHROMATOGRAPHY OF CARBOHYDRATE ACETATES (1962) Canadian Journal of Chemistry, 40, p. 1043
  • Cadenas, Deferrari, (1961) Analyst, 86, p. 132
  • Partridge, (1949) Nature, 164, p. 443
  • Guthrie, (1962) Methods Carbohyd. Chem., 1, p. 440
  • MacFadyen, (1945) J. Biol. Chem., 158, p. 107

Citas:

---------- APA ----------
Deferrari, J.O., Zuazo, B.N. & Gelpi, M.E. (1973) . The reaction of ammonia with acylated disaccharides. XI. The wohl reaction with octa-O-acytylmelibiononitrile. Carbohydrate Research, 30(2), 313-318.
http://dx.doi.org/10.1016/S0008-6215(00)81817-0
---------- CHICAGO ----------
Deferrari, J.O., Zuazo, B.N., Gelpi, M.E. "The reaction of ammonia with acylated disaccharides. XI. The wohl reaction with octa-O-acytylmelibiononitrile" . Carbohydrate Research 30, no. 2 (1973) : 313-318.
http://dx.doi.org/10.1016/S0008-6215(00)81817-0
---------- MLA ----------
Deferrari, J.O., Zuazo, B.N., Gelpi, M.E. "The reaction of ammonia with acylated disaccharides. XI. The wohl reaction with octa-O-acytylmelibiononitrile" . Carbohydrate Research, vol. 30, no. 2, 1973, pp. 313-318.
http://dx.doi.org/10.1016/S0008-6215(00)81817-0
---------- VANCOUVER ----------
Deferrari, J.O., Zuazo, B.N., Gelpi, M.E. The reaction of ammonia with acylated disaccharides. XI. The wohl reaction with octa-O-acytylmelibiononitrile. Carbohydr. Res. 1973;30(2):313-318.
http://dx.doi.org/10.1016/S0008-6215(00)81817-0