Artículo
Abstract:
Various tetra-O-acetyl-D-hexopyranoses were known to undergo acetyl migration upon methylation with Purdie's reagents; thus, 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose, 1,2,3,6-tetra-O-acetyl-β-D-glucopyranose, and 1,3,4,6-tetra-O-acetyl-β-D-glucopyranose and its α anomer are converted into methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside when methylated with methyl iodide and silver oxide. It is now found that, when each of the above compounds is treated with diazomethane-boron trifluoride etherate, the methylated product is produced in high yield, with the methyl ether group in the expected position. Under the same conditions, 1,3,4,6-tetra-O-α-D-galactopyranose is converted into the 2-methyl ether without the acetyl migration which had been observed when the tetra-O-acetyl-D-galactopyranose was methylated with Purdie's reagents. The tetra-O-acetyl-O-methyl-D-hexopyranoses were then transformed by deacetylation into the following mono-O-methylhexoses: 2-O-methyl-β-D-glucose, 4-O-methyl-D-glucose, 6-O-methyl-α-D-glucose, and 2-O-methyl-β-D-galactose. © 1966.
Registro:
| Documento: | Artículo |
| Título: | Methylation of carbohydrates bearing base-labile substituents, with diazomethane-boron triflouride etherate. I |
| Autor: | Mastronardi, I.O.; Flematti, S.M.; Deferrari, J.O.; Gros, E.G. |
| Filiación: | Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Perú, 222 Buenos Aires, Argentina |
| Año: | 1966 |
| Volumen: | 3 |
| Número: | 2 |
| Página de inicio: | 177 |
| Página de fin: | 183 |
| DOI: | http://dx.doi.org/10.1016/S0008-6215(00)82048-0 |
| Título revista: | Carbohydrate Research |
| Título revista abreviado: | Carbohydr. Res. |
| ISSN: | 00086215 |
| CODEN: | CRBRA |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v3_n2_p177_Mastronardi |
Citas:
---------- APA ----------
Mastronardi, I.O., Flematti, S.M., Deferrari, J.O. & Gros, E.G. (1966) . Methylation of carbohydrates bearing base-labile substituents, with diazomethane-boron triflouride etherate. I. Carbohydrate Research, 3(2), 177-183.http://dx.doi.org/10.1016/S0008-6215(00)82048-0
---------- CHICAGO ----------
Mastronardi, I.O., Flematti, S.M., Deferrari, J.O., Gros, E.G. "Methylation of carbohydrates bearing base-labile substituents, with diazomethane-boron triflouride etherate. I" . Carbohydrate Research 3, no. 2 (1966) : 177-183.http://dx.doi.org/10.1016/S0008-6215(00)82048-0
---------- MLA ----------
Mastronardi, I.O., Flematti, S.M., Deferrari, J.O., Gros, E.G. "Methylation of carbohydrates bearing base-labile substituents, with diazomethane-boron triflouride etherate. I" . Carbohydrate Research, vol. 3, no. 2, 1966, pp. 177-183.http://dx.doi.org/10.1016/S0008-6215(00)82048-0
---------- VANCOUVER ----------
Mastronardi, I.O., Flematti, S.M., Deferrari, J.O., Gros, E.G. Methylation of carbohydrates bearing base-labile substituents, with diazomethane-boron triflouride etherate. I. Carbohydr. Res. 1966;3(2):177-183.http://dx.doi.org/10.1016/S0008-6215(00)82048-0
