Methylation of carbohydrates bearing base-labile substituents, with diazomethane-boron triflouride etherate. I

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 methy...

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Autores principales: Mastronardi, Irma Olinda, Flematti, Susana María, Deferrari, Jorge O., Gros, Eduardo Gervasio
Publicado: 1966
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v3_n2_p177_Mastronardi
http://hdl.handle.net/20.500.12110/paper_00086215_v3_n2_p177_Mastronardi
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id paper:paper_00086215_v3_n2_p177_Mastronardi
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spelling paper:paper_00086215_v3_n2_p177_Mastronardi2023-06-08T14:33:05Z Methylation of carbohydrates bearing base-labile substituents, with diazomethane-boron triflouride etherate. I Mastronardi, Irma Olinda Flematti, Susana María Deferrari, Jorge O. Gros, Eduardo Gervasio 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. Fil:Mastronardi, I.O. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Flematti, S.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Deferrari, J.O. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Gros, E.G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 1966 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v3_n2_p177_Mastronardi http://hdl.handle.net/20.500.12110/paper_00086215_v3_n2_p177_Mastronardi
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
description 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.
author Mastronardi, Irma Olinda
Flematti, Susana María
Deferrari, Jorge O.
Gros, Eduardo Gervasio
spellingShingle Mastronardi, Irma Olinda
Flematti, Susana María
Deferrari, Jorge O.
Gros, Eduardo Gervasio
Methylation of carbohydrates bearing base-labile substituents, with diazomethane-boron triflouride etherate. I
author_facet Mastronardi, Irma Olinda
Flematti, Susana María
Deferrari, Jorge O.
Gros, Eduardo Gervasio
author_sort Mastronardi, Irma Olinda
title Methylation of carbohydrates bearing base-labile substituents, with diazomethane-boron triflouride etherate. I
title_short Methylation of carbohydrates bearing base-labile substituents, with diazomethane-boron triflouride etherate. I
title_full Methylation of carbohydrates bearing base-labile substituents, with diazomethane-boron triflouride etherate. I
title_fullStr Methylation of carbohydrates bearing base-labile substituents, with diazomethane-boron triflouride etherate. I
title_full_unstemmed Methylation of carbohydrates bearing base-labile substituents, with diazomethane-boron triflouride etherate. I
title_sort methylation of carbohydrates bearing base-labile substituents, with diazomethane-boron triflouride etherate. i
publishDate 1966
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v3_n2_p177_Mastronardi
http://hdl.handle.net/20.500.12110/paper_00086215_v3_n2_p177_Mastronardi
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AT deferrarijorgeo methylationofcarbohydratesbearingbaselabilesubstituentswithdiazomethaneborontriflourideetheratei
AT groseduardogervasio methylationofcarbohydratesbearingbaselabilesubstituentswithdiazomethaneborontriflourideetheratei
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