Artículo
Gelpi, M.E.; Deferrari, J.O.; Cadenas, R.A. "Methylation of reducing carbohydrates. Permethylated derivatives of melibiose [O-α-D-galactopyranosyl-(1 → 6)-D-glucopyranose]" (1971) Journal of the Chemical Society C: Organic Chemistry:3354-3357
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Abstract:
Methylation in methanol of α-melibiose and octa-O-acetyl-β- melibiose with ethereal diazomethane, and subsequent permethylation (methyl iodide-barium oxide), gave methyl hepta-O-methyl-β-melibiopyranoside (IV). When α-melibiose was methylated with methyl iodide and barium oxide, a mixture of furanose and pyranose isomers was obtained, from which pure methyl hepta-O-methyl-α-melibiofuranoside [methyl hepta-O-methyl-O-α-D- galactopyranosyl-(1 → 6)-α-D-glucofuranose] (I) was isolated. The preparation of methyl hepta-O-methyl-β-melibiofuranoside (II) is reported.
Registro:
| Documento: | Artículo |
| Título: | Methylation of reducing carbohydrates. Permethylated derivatives of melibiose [O-α-D-galactopyranosyl-(1 → 6)-D-glucopyranose] |
| Autor: | Gelpi, M.E.; Deferrari, J.O.; Cadenas, R.A. |
| Filiación: | Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Argentina Departamento de Química, Facultad de Agronomía y Veterinaria, Universidad de Buenos Aires, Argentina |
| Año: | 1971 |
| Página de inicio: | 3354 |
| Página de fin: | 3357 |
| DOI: | http://dx.doi.org/10.1039/J39710003354 |
| Título revista: | Journal of the Chemical Society C: Organic Chemistry |
| ISSN: | 00224952 |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00224952_v_n_p3354_Gelpi |
Referencias:
- Walker, H.G., Gee, M., Jr., McCready, R.M., (1962) J. Org. Chem., 27, p. 2100
- Ferguson, A.C., Haines, A.H., (1969) J. Chem. Soc. (C), p. 2372
- Kuhn, R., Baer, H.H., Seeliger, A., (1958) Annalen, 611, p. 236
- Schiubach, H.H., Rauchenberger, W., (1925) Ber., 58, p. 1184
- Charlton, W., Haworth, W.N., Hickinbottom, W.J., (1927) J. Chem. Soc., p. 1527
- Zanlungo, A.B., Deferrari, J.O., Cadenas, R.A., (1969) Anales Asoc. Quím. Argentina, 57, p. 51
- Bredereck, H., Sieber, R., Kamphenkel, L., (1956) Chem. Ber., 89, p. 1169
- Klyne, W., (1950) Biochem. J., 47, p. XLI
- Staněk, J., (1956) Chem. and Ind., p. 488
- Staněk, J., (1957) Nature, 179, p. 97
- Birch, G.G., Cowell, N.D., (1967) Carbohyd. Res., 5, p. 232
- Bell, D.J., (1940) J. Chem. Soc., p. 1543
- Micheel, F., Litmann, O., (1928) Annalen, 466, p. 115
- Irvine, J.C., Cameron, A., (1905) J. Chem. Soc., 87, p. 900
- Purdie, T., Irvine, J.C., (1904) J. Chem. Soc., 85, p. 1049
- Haworth, W.N., Porter, C.R., Waine, A.C., (1932) J. Chem. Soc., p. 2254
- Hess, K., Heumann, K.E., (1939) Ber., 72, p. 149
- Hudson, C.S., (1916) J. Amer. Chem. Soc., 38, p. 1566
- Jones, J.B., Price, P., (1969) Chem. Comm., p. 1478
- Partridge, S.M., (1949) Nature, 164, p. 443
- Guthrie, R.D., (1962) Methods in Carbohydrate Chemistry, 1, p. 435. , In, eds. R. L. Whistler and M. L. Wolfrom, Academic Press, New York
- Mac. Fadyen, P.A., (1945) J. Biol. Chem., 158, p. 107
- Arndt, F., (1943) Org. Synth., 2, p. 165. , Coll
- Fletcher, H.G., Diehl, H.W., Jr., (1952) J. Amer. Chem. Soc., 74, p. 5774
- Scheiber, C., Mittelmeier, H., (1890) Ber., 2, p. 1438
Citas:
---------- APA ----------
Gelpi, M.E., Deferrari, J.O. & Cadenas, R.A. (1971) . Methylation of reducing carbohydrates. Permethylated derivatives of melibiose [O-α-D-galactopyranosyl-(1 → 6)-D-glucopyranose]. Journal of the Chemical Society C: Organic Chemistry, 3354-3357.http://dx.doi.org/10.1039/J39710003354
---------- CHICAGO ----------
Gelpi, M.E., Deferrari, J.O., Cadenas, R.A. "Methylation of reducing carbohydrates. Permethylated derivatives of melibiose [O-α-D-galactopyranosyl-(1 → 6)-D-glucopyranose]" . Journal of the Chemical Society C: Organic Chemistry (1971) : 3354-3357.http://dx.doi.org/10.1039/J39710003354
---------- MLA ----------
Gelpi, M.E., Deferrari, J.O., Cadenas, R.A. "Methylation of reducing carbohydrates. Permethylated derivatives of melibiose [O-α-D-galactopyranosyl-(1 → 6)-D-glucopyranose]" . Journal of the Chemical Society C: Organic Chemistry, 1971, pp. 3354-3357.http://dx.doi.org/10.1039/J39710003354
---------- VANCOUVER ----------
Gelpi, M.E., Deferrari, J.O., Cadenas, R.A. Methylation of reducing carbohydrates. Permethylated derivatives of melibiose [O-α-D-galactopyranosyl-(1 → 6)-D-glucopyranose]. 1971:3354-3357.http://dx.doi.org/10.1039/J39710003354
