Synthesis of 4-aminomethyl-tetrahydrofuran-2-carboxylates with 2,4-cis and 2,4-trans relationships
Templated tetrahydrofuran-based γ-azido esters were prepared with the C-2 and C-4 functionalities in cis and trans relative configurations. This was achieved by ring contraction of the suitably protected 2-O-triflates of pentono-1,5-lactones (d-ribose and l-arabinose) with subsequent introduction of...
| Prif Awduron: | , , , , , , |
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| Fformat: | Journal article |
| Iaith: | English |
| Cyhoeddwyd: |
2006
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| _version_ | 1826282773227241472 |
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| author | Edwards, A Sanjayan, G Hachisu, S Soengas, R Stewart, A Tranter, G Fleet, G |
| author_facet | Edwards, A Sanjayan, G Hachisu, S Soengas, R Stewart, A Tranter, G Fleet, G |
| author_sort | Edwards, A |
| collection | OXFORD |
| description | Templated tetrahydrofuran-based γ-azido esters were prepared with the C-2 and C-4 functionalities in cis and trans relative configurations. This was achieved by ring contraction of the suitably protected 2-O-triflates of pentono-1,5-lactones (d-ribose and l-arabinose) with subsequent introduction of the azide via the 4-O-triflate. Access to a corresponding β-azido ester was achieved in good yield. Little elimination product was observed by introduction of the azide via the 3-O-triflate. These azido esters are scaffolds, which may be predisposed to adopt secondary structural motifs, for example, for use as peptidomimetics; they may also be utilised for the preparation of stereodiverse compound libraries. © 2006 Elsevier Ltd. All rights reserved. |
| first_indexed | 2024-03-07T00:48:54Z |
| format | Journal article |
| id | oxford-uuid:85ab9b6d-45c6-4c4c-8d49-c7b007060c79 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T00:48:54Z |
| publishDate | 2006 |
| record_format | dspace |
| spelling | oxford-uuid:85ab9b6d-45c6-4c4c-8d49-c7b007060c792022-03-26T21:59:09ZSynthesis of 4-aminomethyl-tetrahydrofuran-2-carboxylates with 2,4-cis and 2,4-trans relationshipsJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:85ab9b6d-45c6-4c4c-8d49-c7b007060c79EnglishSymplectic Elements at Oxford2006Edwards, ASanjayan, GHachisu, SSoengas, RStewart, ATranter, GFleet, GTemplated tetrahydrofuran-based γ-azido esters were prepared with the C-2 and C-4 functionalities in cis and trans relative configurations. This was achieved by ring contraction of the suitably protected 2-O-triflates of pentono-1,5-lactones (d-ribose and l-arabinose) with subsequent introduction of the azide via the 4-O-triflate. Access to a corresponding β-azido ester was achieved in good yield. Little elimination product was observed by introduction of the azide via the 3-O-triflate. These azido esters are scaffolds, which may be predisposed to adopt secondary structural motifs, for example, for use as peptidomimetics; they may also be utilised for the preparation of stereodiverse compound libraries. © 2006 Elsevier Ltd. All rights reserved. |
| spellingShingle | Edwards, A Sanjayan, G Hachisu, S Soengas, R Stewart, A Tranter, G Fleet, G Synthesis of 4-aminomethyl-tetrahydrofuran-2-carboxylates with 2,4-cis and 2,4-trans relationships |
| title | Synthesis of 4-aminomethyl-tetrahydrofuran-2-carboxylates with 2,4-cis and 2,4-trans relationships |
| title_full | Synthesis of 4-aminomethyl-tetrahydrofuran-2-carboxylates with 2,4-cis and 2,4-trans relationships |
| title_fullStr | Synthesis of 4-aminomethyl-tetrahydrofuran-2-carboxylates with 2,4-cis and 2,4-trans relationships |
| title_full_unstemmed | Synthesis of 4-aminomethyl-tetrahydrofuran-2-carboxylates with 2,4-cis and 2,4-trans relationships |
| title_short | Synthesis of 4-aminomethyl-tetrahydrofuran-2-carboxylates with 2,4-cis and 2,4-trans relationships |
| title_sort | synthesis of 4 aminomethyl tetrahydrofuran 2 carboxylates with 2 4 cis and 2 4 trans relationships |
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