Please use this identifier to cite or link to this item: https://hdl.handle.net/2440/102092
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dc.contributor.authorStockton, K.-
dc.contributor.authorGreatrex, B.-
dc.contributor.authorTaylor, D.-
dc.date.issued2014-
dc.identifier.citationJournal of Organic Chemistry, 2014; 79(11):5088-5096-
dc.identifier.issn0022-3263-
dc.identifier.issn1520-6904-
dc.identifier.urihttp://hdl.handle.net/2440/102092-
dc.description.abstractA synthesis of carbocyclic sugars from carbohydrate-derived dialdehydes using organocatalysis has been developed. Sorbitol, mannitol, and galactitol were converted via 1,6-tritylation, perbenzylation or permethylation, detritylation, and Swern oxidation into 2,3,4,5-tetra-O-alkyl-dialdoses that were cyclized via the benzoin reaction promoted by a triazolium carbene. Manno- and galacto-configured dialdehydes gave predominantly single inosose stereoisomers in up to 75% yield if the mixture was acetylated prior to isolation while the gluco-dialdehyde afforded a mixture of three stereoisomers in 61% overall yield. The inososes were stereospecifically reduced using sodium borohydride and then deprotected to give allo- and epi-inositol in good yield that confirmed the structural and stereochemical assignments.-
dc.description.statementofresponsibilityKieran P. Stockton, Ben W. Greatrex, and Dennis K. Taylor-
dc.language.isoen-
dc.publisherAmerican Chemical Society-
dc.rights© 2014 American Chemical Society-
dc.titleSynthesis of allo-and epi-inositol via the NHC-catalyzed carbocyclization of carbohydrate-derived dialdehydes-
dc.typeJournal article-
dc.identifier.doi10.1021/jo500645z-
pubs.publication-statusPublished-
dc.identifier.orcidTaylor, D. [0000-0002-3302-4610] [0000-0002-4274-3983] [0000-0003-0633-7424]-
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