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(2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol

Bennett, Jack
; 
Murphy, Paul V.
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http://hdl.handle.net/10379/16435
 https://doi.org/10.13025/15102
Publication Date
2020-06-03
Keywords
glucose, tetrahydropyran, deprotection, cyclisation, functionalized scaffold
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Article
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Bennett, Jack, & Murphy, Paul V. (2020). (2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol. Molbank, 2020(2), M1140. doi:10.3390/M1140
Abstract
(2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol was isolated in 18% after treating the glucose derived (5R,6S,7R)-5,6,7-tris[(triethylsilyl)oxy]nona-1,8-dien-4-one with (1S)-(+)-10-camphorsulfonic acid (CSA). The one-pot formation of the title compound involved triethylsilyl (TES) removal, alkene isomerization, intramolecular conjugate addition and ketal formation. The compound was characterized by 1H and 13C NMR spectroscopy, ESI mass spectrometry and IR spectroscopy. NMR spectroscopy was used to establish the product structure, including the conformation of its tetrahydropyran ring.
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MDPI
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Attribution-NonCommercial-NoDerivs 3.0 Ireland
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School of Biological and Chemical Sciences (Scholarly Articles)