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[Synthetic studies of polyene macrolide antibiotics. 3. Hydrogenation of methyl-6-deoxy-2,3-O-isopropylidene-4-methylene- alpha-L-lyxo-hexopyranoside]. 1987

A Iu Romanovich, and O S Chizhov, and A F Sviridov

Experimental conditions of hydrogenation of the title compound are found (excess of Raney catalyst in benzene solution, 5 degrees C, 2h) to afford methyl 4,6-dideoxy-2,3-O-isopropylidene-4-C-methyl-alpha-L-mannopyranoside, the key intermediate in the synthesis of C33-C38 fragment of amphotericin B, with the yield as high as 57%.

UI MeSH Term Description Entries
D008759 Methylglycosides
D011090 Polyenes Hydrocarbons with more than one double bond. They are a reduced form of POLYYNES. Cumulenes
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.
D006865 Hydrogenation Addition of hydrogen to a compound, especially to an unsaturated fat or fatty acid. (From Stedman, 26th ed) Hydrogenations
D000666 Amphotericin B Macrolide antifungal antibiotic produced by Streptomyces nodosus obtained from soil of the Orinoco river region of Venezuela. Amphocil,Amphotericin,Amphotericin B Cholesterol Dispersion,Amphotericin B Colloidal Dispersion,Fungizone
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
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

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