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https://hdl.handle.net/2440/47351
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dc.contributor.author | Wilkinson, K. | - |
dc.contributor.author | Elsey, G. | - |
dc.contributor.author | Prager, R. | - |
dc.contributor.author | Tanaka, T. | - |
dc.contributor.author | Sefton, M. | - |
dc.date.issued | 2004 | - |
dc.identifier.citation | Tetrahedron: the international journal for the rapid publication of full original research papers and critical reviews in organic chemistr, 2004; 60(29):6091-6100 | - |
dc.identifier.issn | 0040-4020 | - |
dc.identifier.uri | http://hdl.handle.net/2440/47351 | - |
dc.description | Copyright © 2004 Elsevier Ltd. All rights reserved. | - |
dc.description.abstract | The β-D-glucopyranosides of all four stereoisomers of 3-methyl-4-hydroxyoctanoic acid have been prepared. The (3S,4S) and (3R,4R) species were prepared from cis-5-n-butyl-4-methyl-4,5-dihydro-2(3H)-furanone (cis-oak lactone) by a process involving ring-opening with base and protection of the carboxyl function as its benzyl ester. The glucose unit was introduced by a modified Koenigs–Knorr procedure. A different strategy was necessary for synthesis of the (3S,4R) and (3R,4S) compounds. This was based on the reductive ring-opening of trans-oak lactone and subsequent protection of the primary alcohol as its t-butyldiphenylsilyl ether. Separation of the individual glucosides was effected by preparative thin layer chromatography. Those corresponding to the nature-identical isomers of oak lactone have been shown to produce oak lactone under both acidic hydrolysis and pyrolysis conditions. The galloyl-β-D-glucoside of the cis-species, obtained as a natural isolate from the wood of Platycarya strobilacea, was also found to produce cis-oak lactone upon both acid hydrolysis and pyrolysis. Both the nature-identical (4S,5S) cis-oak lactone and its non-natural (4R,5R) enantiomer have been prepared from their corresponding glycosides and their aroma thresholds in white wine were determined to be 23 and 82 μg/L (ppb) respectively. The aroma threshold of the nature-identical isomer in a red wine was 46 μg/L. | - |
dc.description.statementofresponsibility | Kerry L. Wilkinson, Gordon M. Elsey, Rolf H. Prager, Takashi Tanaka and Mark A. Sefton | - |
dc.description.uri | http://www.elsevier.com/wps/find/journaldescription.cws_home/942/description#description | - |
dc.language.iso | en | - |
dc.publisher | Pergamon-Elsevier Science Ltd | - |
dc.source.uri | http://dx.doi.org/10.1016/j.tet.2004.05.070 | - |
dc.subject | Oak lactone | - |
dc.subject | Glycosides | - |
dc.subject | Hydrolysis | - |
dc.subject | Pyrolysis | - |
dc.subject | β-Glucosidase | - |
dc.subject | Aroma thresholds | - |
dc.title | Precursors to oak lactone. Part 2: Synthesis separation and cleavage of several β-D-glucopyranosides of 3-methyl-4-hydroxyoctanoic acid | - |
dc.title.alternative | Precursors to oak lactone. Part 2: Synthesis separation and cleavage of several beta-D-glucopyranosides of 3-methyl-4-hydroxyoctanoic acid | - |
dc.type | Journal article | - |
dc.identifier.doi | 10.1016/j.tet.2004.05.070 | - |
pubs.publication-status | Published | - |
dc.identifier.orcid | Wilkinson, K. [0000-0001-6724-9837] | - |
Appears in Collections: | Agriculture, Food and Wine publications Aurora harvest |
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