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Synthesis of oligosaccharins: a chemical synthesis of propyl O-beta-D-galactopyranosyl-(1----2)-O-alpha-D-xylopyranosyl-(1----6)- O-beta-D-glucopyranosyl-(1----4)-beta-D-glucopyranoside. 1990

A Wotovic, and J C Jacquinet, and P Sinaÿ
Laboratoire de Biochimie Structurale, U.R.A. 499, U.F.R.-Faculté des Sciences, Université d'Orléans, France.

Condensation of allyl 3,4-di-O-benzyl-beta-D-xylopyranoside with 2-O-acetyl-3,4,6-tri-O-benzyl-alpha-D-galactopyranosyl chloride in dichloromethane in the presence of silver triflate gave allyl 2-O-(2-O-acetyl-3,4-6-tri-O-benzyl-beta-D-galactopyranosyl)-3,4-di-O benzyl-beta-D-xylopyranoside (7, 83%). Compound 7 was converted in five steps into 2-O-(2-O-acetyl-3,4-6-tri-O-benzyl-beta-D-xylopyranosyl bromide (13), which was condensed immediately with allyl 2,3,6-tri-O-acetyl-4-O-(2,3,di-O-acetyl-beta-D-glucopyranosyl)-beta-D- glucopyranoside to give crystalline allyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-beta-D-galactopyranosyl)- (1----2)-O-(3,4,-di-O-benzyl-alpha-D-xylopyranosyl)-(1----6)-O-(2,3,-di- O-acetyl-beta-D-glucopyranosyl)-(1----4)-2,3,6-tri-O-acetyl-beta-D-gluco pyranoside (23, 50%). O-Deacylation of 23 followed by catalytic hydrogenolysis gave the title glycoside.

UI MeSH Term Description Entries
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
D009844 Oligosaccharides Carbohydrates consisting of between two (DISACCHARIDES) and ten MONOSACCHARIDES connected by either an alpha- or beta-glycosidic link. They are found throughout nature in both the free and bound form. Oligosaccharide
D010944 Plants Multicellular, eukaryotic life forms of kingdom Plantae. Plants acquired chloroplasts by direct endosymbiosis of CYANOBACTERIA. They are characterized by a mainly photosynthetic mode of nutrition; essentially unlimited growth at localized regions of cell divisions (MERISTEMS); cellulose within cells providing rigidity; the absence of organs of locomotion; absence of nervous and sensory systems; and an alternation of haploid and diploid generations. It is a non-taxonomical term most often referring to LAND PLANTS. In broad sense it includes RHODOPHYTA and GLAUCOPHYTA along with VIRIDIPLANTAE. Plant
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
D006027 Glycosides Any compound that contains a constituent sugar, in which the hydroxyl group attached to the first carbon is substituted by an alcoholic, phenolic, or other group. They are named specifically for the sugar contained, such as glucoside (glucose), pentoside (pentose), fructoside (fructose), etc. Upon hydrolysis, a sugar and nonsugar component (aglycone) are formed. (From Dorland, 28th ed; From Miall's Dictionary of Chemistry, 5th ed) Glycoside
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular

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