Synthesis of New Unsaturated Polyether Macrodiolides Based on (7<i>Z</i>,11<i>Z</i>)-Octadeca-7,11-Diene-1,18-Dioic Acid
Stereoselective synthesis of (7<i>Z</i>,11<i>Z</i>)-octadeca-7,11-diene-1,18-dioic acid was carried out using a homo-cyclomagnesiation reaction of 2-(nona-7,8-dien-1-yloxy)tetrahydro-2<i>H</i>-pyran. After Steglisch esterification of the synthesized acid and polye...
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MDPI AG
2023-11-01
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| author | Ilgiz Islamov Ilgam Gaisin Usein Dzhemilev |
| author_facet | Ilgiz Islamov Ilgam Gaisin Usein Dzhemilev |
| author_sort | Ilgiz Islamov |
| collection | DOAJ |
| description | Stereoselective synthesis of (7<i>Z</i>,11<i>Z</i>)-octadeca-7,11-diene-1,18-dioic acid was carried out using a homo-cyclomagnesiation reaction of 2-(nona-7,8-dien-1-yloxy)tetrahydro-2<i>H</i>-pyran. After Steglisch esterification of the synthesized acid and polyester acetylenes in the presence of DCC and DMAP, the corresponding diesters were synthesized in good yields (67–75%). Based on symmetric diesters with terminal triple bonds, polyether macrodiolides containing conjugated triple bonds and pharmacophoric <i>cis,cis</i>-1,5-diene fragments in their structure were synthesized for the first time. |
| format | Article |
| id | doaj-art-25895f2c323b4e969f79a8a2aaf2559e |
| institution | Kabale University |
| issn | 2673-4583 |
| language | English |
| publishDate | 2023-11-01 |
| publisher | MDPI AG |
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| series | Chemistry Proceedings |
| spelling | doaj-art-25895f2c323b4e969f79a8a2aaf2559e2024-12-27T14:17:29ZengMDPI AGChemistry Proceedings2673-45832023-11-011417010.3390/ecsoc-27-16047Synthesis of New Unsaturated Polyether Macrodiolides Based on (7<i>Z</i>,11<i>Z</i>)-Octadeca-7,11-Diene-1,18-Dioic AcidIlgiz Islamov0Ilgam Gaisin1Usein Dzhemilev2Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa 450075, RussiaInstitute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa 450075, RussiaN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospekt, 47, Moscow 119991, RussiaStereoselective synthesis of (7<i>Z</i>,11<i>Z</i>)-octadeca-7,11-diene-1,18-dioic acid was carried out using a homo-cyclomagnesiation reaction of 2-(nona-7,8-dien-1-yloxy)tetrahydro-2<i>H</i>-pyran. After Steglisch esterification of the synthesized acid and polyester acetylenes in the presence of DCC and DMAP, the corresponding diesters were synthesized in good yields (67–75%). Based on symmetric diesters with terminal triple bonds, polyether macrodiolides containing conjugated triple bonds and pharmacophoric <i>cis,cis</i>-1,5-diene fragments in their structure were synthesized for the first time.https://www.mdpi.com/2673-4583/14/1/70homo-cyclomagnesiation1,5-dienoic compoundsoxidative coupling1,3-diynesmacrodiolides |
| spellingShingle | Ilgiz Islamov Ilgam Gaisin Usein Dzhemilev Synthesis of New Unsaturated Polyether Macrodiolides Based on (7<i>Z</i>,11<i>Z</i>)-Octadeca-7,11-Diene-1,18-Dioic Acid Chemistry Proceedings homo-cyclomagnesiation 1,5-dienoic compounds oxidative coupling 1,3-diynes macrodiolides |
| title | Synthesis of New Unsaturated Polyether Macrodiolides Based on (7<i>Z</i>,11<i>Z</i>)-Octadeca-7,11-Diene-1,18-Dioic Acid |
| title_full | Synthesis of New Unsaturated Polyether Macrodiolides Based on (7<i>Z</i>,11<i>Z</i>)-Octadeca-7,11-Diene-1,18-Dioic Acid |
| title_fullStr | Synthesis of New Unsaturated Polyether Macrodiolides Based on (7<i>Z</i>,11<i>Z</i>)-Octadeca-7,11-Diene-1,18-Dioic Acid |
| title_full_unstemmed | Synthesis of New Unsaturated Polyether Macrodiolides Based on (7<i>Z</i>,11<i>Z</i>)-Octadeca-7,11-Diene-1,18-Dioic Acid |
| title_short | Synthesis of New Unsaturated Polyether Macrodiolides Based on (7<i>Z</i>,11<i>Z</i>)-Octadeca-7,11-Diene-1,18-Dioic Acid |
| title_sort | synthesis of new unsaturated polyether macrodiolides based on 7 i z i 11 i z i octadeca 7 11 diene 1 18 dioic acid |
| topic | homo-cyclomagnesiation 1,5-dienoic compounds oxidative coupling 1,3-diynes macrodiolides |
| url | https://www.mdpi.com/2673-4583/14/1/70 |
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