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, I.O., Flematti, S.M., Deferrari, J.O., Gros, E.G.
Formato: JOUR
Acceso en línea: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
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spelling todo:paper_00086215_v3_n2_p177_Mastronardi2023-10-03T14:07:33Z Methylation of carbohydrates bearing base-labile substituents, with diazomethane-boron triflouride etherate. I Mastronardi, I.O. Flematti, S.M. Deferrari, J.O. Gros, E.G. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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.
format JOUR
author Mastronardi, I.O.
Flematti, S.M.
Deferrari, J.O.
Gros, E.G.
spellingShingle 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
author_facet Mastronardi, I.O.
Flematti, S.M.
Deferrari, J.O.
Gros, E.G.
author_sort Mastronardi, I.O.
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
url http://hdl.handle.net/20.500.12110/paper_00086215_v3_n2_p177_Mastronardi
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AT deferrarijo methylationofcarbohydratesbearingbaselabilesubstituentswithdiazomethaneborontriflourideetheratei
AT groseg methylationofcarbohydratesbearingbaselabilesubstituentswithdiazomethaneborontriflourideetheratei
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