Please use this identifier to cite or link to this item:
https://hdl.handle.net/2440/102092
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dc.contributor.author | Stockton, K. | - |
dc.contributor.author | Greatrex, B. | - |
dc.contributor.author | Taylor, D. | - |
dc.date.issued | 2014 | - |
dc.identifier.citation | Journal of Organic Chemistry, 2014; 79(11):5088-5096 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.issn | 1520-6904 | - |
dc.identifier.uri | http://hdl.handle.net/2440/102092 | - |
dc.description.abstract | A 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.statementofresponsibility | Kieran P. Stockton, Ben W. Greatrex, and Dennis K. Taylor | - |
dc.language.iso | en | - |
dc.publisher | American Chemical Society | - |
dc.rights | © 2014 American Chemical Society | - |
dc.source.uri | http://dx.doi.org/10.1021/jo500645z | - |
dc.title | Synthesis of allo-and epi-inositol via the NHC-catalyzed carbocyclization of carbohydrate-derived dialdehydes | - |
dc.type | Journal article | - |
dc.identifier.doi | 10.1021/jo500645z | - |
pubs.publication-status | Published | - |
dc.identifier.orcid | Taylor, D. [0000-0002-3302-4610] [0000-0002-4274-3983] [0000-0003-0633-7424] | - |
Appears in Collections: | Agriculture, Food and Wine publications Aurora harvest 3 |
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