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Addition of lithiated C-nucleophiles to 2,3-O-isopropylidene-D-erythronolactone: stereoselective formation of a furanose C-disaccharide. 2003

Jason L McCartney, and Christopher T Meta, and Robert M Cicchillo, and Matthew D Bernardina, and Timothy R Wagner, and Peter Norris
Department of Chemistry, Youngstown State University, 1 University Plaza, Youngstown, Ohio 44555-3663, USA.

Addition of PhLi and lithiated dithianes to 2,3-O-isopropylidene-D-erythronolactone affords lactols, which are reduced with Et3SiH to the corresponding C-glycosides, the structures of two of which have been solved by X-ray diffraction. The use of a d-ribose-derived lithiated dithiane nucleophile in this chemistry allows for the convenient construction of a furanose C-disaccharide.

UI MeSH Term Description Entries
D007783 Lactones Cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure. Large cyclic lactones of over a dozen atoms are MACROLIDES. Lactone
D008094 Lithium An element in the alkali metals family. It has the atomic symbol Li, atomic number 3, and atomic weight [6.938; 6.997]. Salts of lithium are used in treating BIPOLAR DISORDER. Lithium-7,Lithium 7
D009942 Organometallic Compounds A class of compounds of the type R-M, where a C atom is joined directly to any other element except H, C, N, O, F, Cl, Br, I, or At. (Grant & Hackh's Chemical Dictionary, 5th ed) Metallo-Organic Compound,Metallo-Organic Compounds,Metalloorganic Compound,Organometallic Compound,Metalloorganic Compounds,Compound, Metallo-Organic,Compound, Metalloorganic,Compound, Organometallic,Compounds, Metallo-Organic,Compounds, Metalloorganic,Compounds, Organometallic,Metallo Organic Compound,Metallo Organic Compounds
D011807 Quinolizines
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
D004187 Disaccharides Oligosaccharides containing two monosaccharide units linked by a glycosidic bond. Disaccharide
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
D012266 Ribose A pentose active in biological systems usually in its D-form. D-Ribose,D Ribose
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D013457 Sulfur Compounds Inorganic or organic compounds that contain sulfur as an integral part of the molecule. Sulfur Compound,Compound, Sulfur,Compounds, Sulfur

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