BIOMAT Database Logo BIOMAT Database Logo

Synthesis of methyl O-(3-deoxy-3-fluoro-beta-D-galactopyranosyl)-(1----6)-beta-D- galactopyranoside and methyl O-(3-deoxy-3-fluoro-beta-D-galactopyranosyl)-(1----6)-O-beta-D- galactopyranosyl-(1----6)-beta-D-galactopyranoside. 1985

P Kovác, and H J Yeh, and C P Glaudemans

Condensation of 2,4,6-tri-O-acetyl-3-deoxy-3-fluoro-alpha-D-galactopyranosyl bromide (3) with methyl 2,3,4-tri-O-acetyl-beta-D-galactopyranoside (4) gave a fully acetylated (1----6)-beta-D-galactobiose fluorinated at the 3'-position which was deacetylated to give the title disaccharide. The corresponding trisaccharide was obtained by reaction of 4 with 2,3,4-tri-O-acetyl-6-O-chloracetyl-alpha-D-galactopyranosyl bromide (5), dechloroacetylation of the formed methyl O-(2,3,4-tri-O-acetyl-6-O-chloroacetyl-beta-D-galactopyranosyl)-(1----6) -2,3, 4-tri-O-acetyl-beta-D-galactopyranoside to give methyl O-(2,3,4-tri-O-acetyl-beta-D-galactopyranosyl)-(1----6)-2,3, 4-tri-O-acetyl-beta-D-galactopyranoside (14), condensation with 3, and deacetylation. Dechloroacetylation of methyl O-(2,3,4-tri-O-acetyl-6-O-chloroacetyl-beta-D-galactopyranosyl)-(1----6) -O-(2,3 , 4-tri-O-acetyl-beta-D-galactopyranosyl)-(1----6)-2,3,4-tri-O-acetyl-beta -D- galactopyranoside, obtained by condensation of disaccharide 14 with bromide 5, was accompanied by extensive acetyl migration giving a mixture of products. These were deacetylated to give, crystalline for the first time, the methyl beta-glycoside of (1----6)-beta-D-galactotriose in high yield. The structures of the target compounds were confirmed by 500-MHz, 2D, 1H- and conventional 13C- and 19F-n.m.r. spectroscopy.

UI MeSH Term Description Entries
D007202 Indicators and Reagents Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499) Indicator,Reagent,Reagents,Indicators,Reagents and Indicators
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D002236 Carbohydrate Conformation The characteristic 3-dimensional shape of a carbohydrate. Carbohydrate Linkage,Carbohydrate Conformations,Carbohydrate Linkages,Conformation, Carbohydrate,Conformations, Carbohydrate,Linkage, Carbohydrate,Linkages, Carbohydrate
D002621 Chemistry A basic science concerned with the composition, structure, and properties of matter; and the reactions that occur between substances and the associated energy exchange.
D002855 Chromatography, Thin Layer Chromatography on thin layers of adsorbents rather than in columns. The adsorbent can be alumina, silica gel, silicates, charcoals, or cellulose. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed) Chromatography, Thin-Layer,Thin Layer Chromatography,Chromatographies, Thin Layer,Chromatographies, Thin-Layer,Thin Layer Chromatographies,Thin-Layer Chromatographies,Thin-Layer Chromatography
D004187 Disaccharides Oligosaccharides containing two monosaccharide units linked by a glycosidic bond. Disaccharide
D014312 Trisaccharides Oligosaccharides containing three monosaccharide units linked by glycosidic bonds. Trisaccharide
D055598 Chemical Phenomena The composition, structure, conformation, and properties of atoms and molecules, and their reaction and interaction processes. Chemical Concepts,Chemical Processes,Physical Chemistry Concepts,Physical Chemistry Processes,Physicochemical Concepts,Physicochemical Phenomena,Physicochemical Processes,Chemical Phenomenon,Chemical Process,Physical Chemistry Phenomena,Physical Chemistry Process,Physicochemical Phenomenon,Physicochemical Process,Chemical Concept,Chemistry Process, Physical,Chemistry Processes, Physical,Concept, Chemical,Concept, Physical Chemistry,Concept, Physicochemical,Concepts, Chemical,Concepts, Physical Chemistry,Concepts, Physicochemical,Phenomena, Chemical,Phenomena, Physical Chemistry,Phenomena, Physicochemical,Phenomenon, Chemical,Phenomenon, Physicochemical,Physical Chemistry Concept,Physicochemical Concept,Process, Chemical,Process, Physical Chemistry,Process, Physicochemical,Processes, Chemical,Processes, Physical Chemistry,Processes, Physicochemical

Related Publications

P Kovác, and H J Yeh, and C P Glaudemans
Synthesis of methyl O-(3-deoxy-3-fluoro-beta-D-galactopyranosyl)-(1----6)-O-beta-D- galactopyranosyl-(1----6)-3-deoxy-3-fluoro-beta-D-galactopyranoside and related N.M.R. studies.
July 1985, Carbohydrate research,
P Kovác, and H J Yeh, and C P Glaudemans
Synthesis of benzyl O-(3-O-methyl-beta-D-galactopyranosyl)-(1-->3)-2- acetamido-2-deoxy-alpha-D-galactopyranoside and benzyl O-(beta-D- galactopyranosyl)-(1-->3)-2-acetamido-2-deoxy-6-O-methyl-alpha-D- galactopyranoside as specific acceptors for sialyltransferases.
July 1995, Carbohydrate research,
P Kovác, and H J Yeh, and C P Glaudemans
Synthesis of methyl O-(2-O-methyl-beta-D-galactopyranosyl)-(1----4)-O-(2- acetamido-2-deoxy-beta-D-glucopyranosyl)-(1----3)-beta-D- galactopyranoside and 4-nitrophenyl O-beta-D-galactopyranosyl-(1----4)-O-(2-acetamido-2-deoxy-beta-D- glucopyranosyl)-(1----3)-beta-D-galactopyranoside.
August 1990, Carbohydrate research,
P Kovác, and H J Yeh, and C P Glaudemans
Synthetic receptor analogues: preparation and calculated conformations of the 2-deoxy, 6-O-methyl, 6-deoxy, and 6-deoxy-6-fluoro derivatives of methyl 4-O-alpha-D-galactopyranosyl-beta-D-galactopyranoside (methyl beta-D-galabioside).
May 1988, Carbohydrate research,
P Kovác, and H J Yeh, and C P Glaudemans
Synthesis of 2-acetamido-2-deoxy-6-O-beta-D-galactopyranosyl-D-galactopyranose and o-nitrophenyl 2-acetamido-2-deoxy-6-O-beta-D-galactopyranosyl -alpha-D-galactopyranoside.
August 1984, Carbohydrate research,
P Kovác, and H J Yeh, and C P Glaudemans
Synthetic mucin fragments. Methyl 6-O-(2-acetamido-2-deoxy-beta-D- glucopyranosyl)-beta-D-galactopyranoside, methyl 3,4-di-O-(2-acetamido-2-deoxy- beta-D-glucopyranosyl)-beta-D-galactopyranoside, and methyl O-(2-acetamido-2- deoxy-beta-D-glucopyranosyl)-(1----3)-O-beta-D-galactopyranosyl-(1---- 3)-O-(2- acetamido-2-deoxy-beta-D-glucopyranosyl)-(1----3)-beta-D-galactopyr ano side.
March 1987, Carbohydrate research,
P Kovác, and H J Yeh, and C P Glaudemans
Preparation and calculated conformations of the 2'-, 3'-, 4'-, and 6'-deoxy, 3'-O-methyl, 4'-epi, and 4'- and 6'-deoxy-fluoro derivatives of methyl 4-O-alpha-D-galactopyranosyl-beta-D-galactopyranoside (methyl beta-D-galabioside).
February 1989, Carbohydrate research,
P Kovác, and H J Yeh, and C P Glaudemans
Synthesis and characterization of methyl 6-O-alpha- and -beta-D-galactopyranosyl-beta-D-galactopyranoside.
May 1984, Carbohydrate research,
P Kovác, and H J Yeh, and C P Glaudemans
Synthesis of 2,3-epoxypropyl O-beta-D-galactopyranosyl-(1----6)-beta-D-galactopyranoside.
January 1986, Carbohydrate research,
P Kovác, and H J Yeh, and C P Glaudemans
Efficient and stereoselective synthesis of methyl 3-O-(3,6-anhydro-beta-D-galactopyranosyl)-alpha-D-galactopyranoside and methyl 3,6-anhydro-4-O-beta-D-galactopyranosyl-alpha-D-galactopyranoside.
January 1992, Carbohydrate research,
Copied contents to your clipboard!