Abstract
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.
Publication types
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Carbohydrate Conformation
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Disaccharides / chemical synthesis*
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Disaccharides / chemistry
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Glycosides / chemistry
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Lactones / chemistry*
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Lithium / chemistry*
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Organometallic Compounds / chemistry
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Quinolizines / chemistry
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Ribose / chemistry
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Stereoisomerism
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Sulfur Compounds / chemistry
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X-Ray Diffraction
Substances
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Disaccharides
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Glycosides
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Lactones
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Organometallic Compounds
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Quinolizines
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Sulfur Compounds
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dithiane
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Ribose
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Lithium