Synthesis of the methyl thioglycosides of 2-, 3-, and 4-deoxy-L-fucose. 1994

A Hasegawa, and T Ando, and M Kato, and H Ishida, and M Kiso
Department of Applied Bioorganic Chemistry, Gifu University, Japan.

Methyl thioglycoside derivatives of 2-, 3-, and 4-deoxy-L-fucopyranose have been prepared as glycosyl donors for the synthesis of sialyl Le(x) ganglioside analogues containing modified alpha-L-fucopyranose residues. Reductive dethioacylation of 2-(trimethylsilyl)ethyl 3,4-di-O-benzoyl-2-O-(phenoxy)thiocarbonyl-beta-L-fucopyranoside, prepared from L-fucose in eight steps, gave the 2-deoxy compound, which was transformed via selective removal of the 2-(trimethylsilyl)ethyl group, subsequent acetylation, and displacement of the 1-acetoxy group by a methylthio group, into methyl 3,4-di-O-benzoyl-2,6-dideoxy-1-thio- alpha,beta-L-lyxo-hexopyranoside (11). 2-(Trimethylsilyl)ethyl 2,4-di-O-benzoyl-3-O-(phenoxy)thiocarbonyl-beta- L-fucopyranoside, prepared from the unsubstituted glycoside in four steps, and 2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-4-O-(phenoxy)thiocarbonyl-beta-L-fucopyranoside, similarly prepared in two steps, were transformed via reduction of the (phenoxy)thiocarbonyloxy group, selective removal of the 2-(trimethylsilyl)ethyl group, O-acetylation, displacement of the 1-acetoxy group by a methylthio group as described for 11, and finally replacement of the benzoyl groups by benzyl groups, into the analogous, protected methyl 3- and 4-deoxy-1-thio-beta-L-fucopyranosides.

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
D008969 Molecular Sequence Data Descriptions of specific amino acid, carbohydrate, or nucleotide sequences which have appeared in the published literature and/or are deposited in and maintained by databanks such as GENBANK, European Molecular Biology Laboratory (EMBL), National Biomedical Research Foundation (NBRF), or other sequence repositories. Sequence Data, Molecular,Molecular Sequencing Data,Data, Molecular Sequence,Data, Molecular Sequencing,Sequencing Data, Molecular
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
D009904 Optical Rotation The rotation of linearly polarized light as it passes through various media. Optical Activity,Activity, Optical,Rotation, Optical
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
D002240 Carbohydrate Sequence The sequence of carbohydrates within POLYSACCHARIDES; GLYCOPROTEINS; and GLYCOLIPIDS. Carbohydrate Sequences,Sequence, Carbohydrate,Sequences, Carbohydrate
D005643 Fucose A six-member ring deoxysugar with the chemical formula C6H12O5. It lacks a hydroxyl group on the carbon at position 6 of the molecule. Deoxygalactose,alpha-Fucose,alpha Fucose
D013865 Thioglycosides

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