Regioselective ketalization (dioxane vs dioxolane) study of internal diastereomeric 1,2,3-triol systems obtained from d-pentoses
Ringselective and regioselective acetonide protection of four diastereomeric triol systems (ribo & xylo with 1,3-syn configuration and arabino & lyxo with 1,3-anti configuration) were studied and certain useful generalizations are drawn as follows. Three triol systems i.e. xylo, arab...
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| Format: | Article |
| Language: | English |
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Elsevier
2022-01-01
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| Series: | Results in Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2211715622000601 |
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| author | Chiranjeevi Donthulachitti Yelukala Ramakrishna Ravikumar Shekunti Chandra Kiran Neella |
| author_facet | Chiranjeevi Donthulachitti Yelukala Ramakrishna Ravikumar Shekunti Chandra Kiran Neella |
| author_sort | Chiranjeevi Donthulachitti |
| collection | DOAJ |
| description | Ringselective and regioselective acetonide protection of four diastereomeric triol systems (ribo & xylo with 1,3-syn configuration and arabino & lyxo with 1,3-anti configuration) were studied and certain useful generalizations are drawn as follows. Three triol systems i.e. xylo, arabino and lyxo triol systems have preferred only five membered acetonides (dioxolanes) over six membered acetonides (dioxanes). Selective formation of five membered anti acetonides was noticed when there is a competition between syn and anti acetonide formation. If the acetonides formed from any triol system are either syn or anti, then only allylic acetonides are favoured over non-allylic acetonnides. Only ribo-triol system formed six membered syn acetonides (thermodynamic control). No triol has produced all the three acetonides. All the ring sizes were unambiguously confirmed by employing Evan's 13C NMR method supported by 1H NMR spectroscopy. These chiral building blocks with predefined stereochemistry and multiple functional groups can be potential scaffolds for total synthesis. |
| first_indexed | 2024-04-12T01:40:39Z |
| format | Article |
| id | doaj.art-6018fc94ec4a47c39ae4d4ea26c9eb2d |
| institution | Directory Open Access Journal |
| issn | 2211-7156 |
| language | English |
| last_indexed | 2024-04-12T01:40:39Z |
| publishDate | 2022-01-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Results in Chemistry |
| spelling | doaj.art-6018fc94ec4a47c39ae4d4ea26c9eb2d2022-12-22T03:53:12ZengElsevierResults in Chemistry2211-71562022-01-014100341Regioselective ketalization (dioxane vs dioxolane) study of internal diastereomeric 1,2,3-triol systems obtained from d-pentosesChiranjeevi Donthulachitti0Yelukala Ramakrishna1Ravikumar Shekunti2Chandra Kiran Neella3Dept of M.Sc. 5Yr Integrated Chemistry, Palamuru University, Mahabubnagar, Telangana State 509001, IndiaDept of M.Sc. 5Yr Integrated Chemistry, Palamuru University, Mahabubnagar, Telangana State 509001, IndiaDept of M.Sc. 5Yr Integrated Chemistry, Palamuru University, Mahabubnagar, Telangana State 509001, IndiaDept of Chemistry, Palamuru University, Mahabubnagar, Telangana State 509001, India; Corresponding author.Ringselective and regioselective acetonide protection of four diastereomeric triol systems (ribo & xylo with 1,3-syn configuration and arabino & lyxo with 1,3-anti configuration) were studied and certain useful generalizations are drawn as follows. Three triol systems i.e. xylo, arabino and lyxo triol systems have preferred only five membered acetonides (dioxolanes) over six membered acetonides (dioxanes). Selective formation of five membered anti acetonides was noticed when there is a competition between syn and anti acetonide formation. If the acetonides formed from any triol system are either syn or anti, then only allylic acetonides are favoured over non-allylic acetonnides. Only ribo-triol system formed six membered syn acetonides (thermodynamic control). No triol has produced all the three acetonides. All the ring sizes were unambiguously confirmed by employing Evan's 13C NMR method supported by 1H NMR spectroscopy. These chiral building blocks with predefined stereochemistry and multiple functional groups can be potential scaffolds for total synthesis.http://www.sciencedirect.com/science/article/pii/S2211715622000601Regioselective acetonide protectionSyn/anti acetonidesDioxanesDioxolanes |
| spellingShingle | Chiranjeevi Donthulachitti Yelukala Ramakrishna Ravikumar Shekunti Chandra Kiran Neella Regioselective ketalization (dioxane vs dioxolane) study of internal diastereomeric 1,2,3-triol systems obtained from d-pentoses Results in Chemistry Regioselective acetonide protection Syn/anti acetonides Dioxanes Dioxolanes |
| title | Regioselective ketalization (dioxane vs dioxolane) study of internal diastereomeric 1,2,3-triol systems obtained from d-pentoses |
| title_full | Regioselective ketalization (dioxane vs dioxolane) study of internal diastereomeric 1,2,3-triol systems obtained from d-pentoses |
| title_fullStr | Regioselective ketalization (dioxane vs dioxolane) study of internal diastereomeric 1,2,3-triol systems obtained from d-pentoses |
| title_full_unstemmed | Regioselective ketalization (dioxane vs dioxolane) study of internal diastereomeric 1,2,3-triol systems obtained from d-pentoses |
| title_short | Regioselective ketalization (dioxane vs dioxolane) study of internal diastereomeric 1,2,3-triol systems obtained from d-pentoses |
| title_sort | regioselective ketalization dioxane vs dioxolane study of internal diastereomeric 1 2 3 triol systems obtained from d pentoses |
| topic | Regioselective acetonide protection Syn/anti acetonides Dioxanes Dioxolanes |
| url | http://www.sciencedirect.com/science/article/pii/S2211715622000601 |
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