(2<em>S</em>,3<em>R</em>,6<em>R</em>)-2-[(<em>R</em>)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2<em>H</em>-pyran-3-ol
(2<i>S</i>,3<i>R</i>,6<i>R</i>)-2-[(<i>R</i>)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2<i>H</i>-pyran-3-ol was isolated in 18% after treating the glucose derived (5<i>R</i>,6<i>S</i>,7<i>R</i>)-5...
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| Format: | Article |
| Language: | English |
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MDPI AG
2020-06-01
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| Series: | Molbank |
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| Online Access: | https://www.mdpi.com/1422-8599/2020/2/M1140 |
| _version_ | 1827715632042344448 |
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| author | Jack Bennett Paul V. Murphy |
| author_facet | Jack Bennett Paul V. Murphy |
| author_sort | Jack Bennett |
| collection | DOAJ |
| description | (2<i>S</i>,3<i>R</i>,6<i>R</i>)-2-[(<i>R</i>)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2<i>H</i>-pyran-3-ol was isolated in 18% after treating the glucose derived (5<i>R</i>,6<i>S</i>,7<i>R</i>)-5,6,7-tris[(triethylsilyl)oxy]nona-1,8-dien-4-one with (1<i>S</i>)-(+)-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 <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy, ESI mass spectrometry and IR spectroscopy. NMR spectroscopy was used to establish the product structure, including the conformation of its tetrahydropyran ring. |
| first_indexed | 2024-03-10T19:23:38Z |
| format | Article |
| id | doaj.art-448bbba3ef864b979de0a65539ba1623 |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-03-10T19:23:38Z |
| publishDate | 2020-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-448bbba3ef864b979de0a65539ba16232023-11-20T02:46:11ZengMDPI AGMolbank1422-85992020-06-0120202M114010.3390/M1140(2<em>S</em>,3<em>R</em>,6<em>R</em>)-2-[(<em>R</em>)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2<em>H</em>-pyran-3-olJack Bennett0Paul V. Murphy1School of Chemistry, National University of Ireland, H91 TK33 Galway, IrelandSchool of Chemistry, National University of Ireland, H91 TK33 Galway, Ireland(2<i>S</i>,3<i>R</i>,6<i>R</i>)-2-[(<i>R</i>)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2<i>H</i>-pyran-3-ol was isolated in 18% after treating the glucose derived (5<i>R</i>,6<i>S</i>,7<i>R</i>)-5,6,7-tris[(triethylsilyl)oxy]nona-1,8-dien-4-one with (1<i>S</i>)-(+)-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 <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy, ESI mass spectrometry and IR spectroscopy. NMR spectroscopy was used to establish the product structure, including the conformation of its tetrahydropyran ring.https://www.mdpi.com/1422-8599/2020/2/M1140glucosetetrahydropyrandeprotectioncyclisationfunctionalized scaffold |
| spellingShingle | Jack Bennett Paul V. Murphy (2<em>S</em>,3<em>R</em>,6<em>R</em>)-2-[(<em>R</em>)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2<em>H</em>-pyran-3-ol Molbank glucose tetrahydropyran deprotection cyclisation functionalized scaffold |
| title | (2<em>S</em>,3<em>R</em>,6<em>R</em>)-2-[(<em>R</em>)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2<em>H</em>-pyran-3-ol |
| title_full | (2<em>S</em>,3<em>R</em>,6<em>R</em>)-2-[(<em>R</em>)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2<em>H</em>-pyran-3-ol |
| title_fullStr | (2<em>S</em>,3<em>R</em>,6<em>R</em>)-2-[(<em>R</em>)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2<em>H</em>-pyran-3-ol |
| title_full_unstemmed | (2<em>S</em>,3<em>R</em>,6<em>R</em>)-2-[(<em>R</em>)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2<em>H</em>-pyran-3-ol |
| title_short | (2<em>S</em>,3<em>R</em>,6<em>R</em>)-2-[(<em>R</em>)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2<em>H</em>-pyran-3-ol |
| title_sort | 2 em s em 3 em r em 6 em r em 2 em r em 1 hydroxyallyl 4 4 dimethoxy 6 methyltetrahydro 2 em h em pyran 3 ol |
| topic | glucose tetrahydropyran deprotection cyclisation functionalized scaffold |
| url | https://www.mdpi.com/1422-8599/2020/2/M1140 |
| work_keys_str_mv | AT jackbennett 2emsem3emrem6emrem2emrem1hydroxyallyl44dimethoxy6methyltetrahydro2emhempyran3ol AT paulvmurphy 2emsem3emrem6emrem2emrem1hydroxyallyl44dimethoxy6methyltetrahydro2emhempyran3ol |