Synthesis of Deoxysugars through Manganese-promoted Redox Isomerization
Deoxysugars feature prominently in many bioactive natural products and pharmaceutical compounds. Many synthetic routes towards deoxysugars rely on protecting groups to achieve selective outcomes. Here we report a concise synthetic strategy to access a diverse set of 2- and 4-deoxysugars using a Mn-p...
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| Format: | Thesis |
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Massachusetts Institute of Technology
2022
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| Online Access: | https://hdl.handle.net/1721.1/139107 |
| _version_ | 1811075052564643840 |
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| author | Suh, Carolyn E. |
| author2 | Wendlandt, Alison |
| author_facet | Wendlandt, Alison Suh, Carolyn E. |
| author_sort | Suh, Carolyn E. |
| collection | MIT |
| description | Deoxysugars feature prominently in many bioactive natural products and pharmaceutical compounds. Many synthetic routes towards deoxysugars rely on protecting groups to achieve selective outcomes. Here we report a concise synthetic strategy to access a diverse set of 2- and 4-deoxysugars using a Mn-promoted redox isomerization step that avoids lengthy protecting group manipulations. We determine the resting state of the manganese catalyst to be Mn(II). We demonstrate subsequent derivatizations with the ketone moiety to access branched sugars and amino sugars as well, showcasing the versatility and utility of this method. |
| first_indexed | 2024-09-23T09:59:53Z |
| format | Thesis |
| id | mit-1721.1/139107 |
| institution | Massachusetts Institute of Technology |
| last_indexed | 2024-09-23T09:59:53Z |
| publishDate | 2022 |
| publisher | Massachusetts Institute of Technology |
| record_format | dspace |
| spelling | mit-1721.1/1391072022-01-15T03:56:28Z Synthesis of Deoxysugars through Manganese-promoted Redox Isomerization Suh, Carolyn E. Wendlandt, Alison Massachusetts Institute of Technology. Department of Chemistry Deoxysugars feature prominently in many bioactive natural products and pharmaceutical compounds. Many synthetic routes towards deoxysugars rely on protecting groups to achieve selective outcomes. Here we report a concise synthetic strategy to access a diverse set of 2- and 4-deoxysugars using a Mn-promoted redox isomerization step that avoids lengthy protecting group manipulations. We determine the resting state of the manganese catalyst to be Mn(II). We demonstrate subsequent derivatizations with the ketone moiety to access branched sugars and amino sugars as well, showcasing the versatility and utility of this method. S.M. 2022-01-14T14:50:20Z 2022-01-14T14:50:20Z 2021-06 2021-06-16T17:34:10.697Z Thesis https://hdl.handle.net/1721.1/139107 In Copyright - Educational Use Permitted Copyright MIT http://rightsstatements.org/page/InC-EDU/1.0/ application/pdf Massachusetts Institute of Technology |
| spellingShingle | Suh, Carolyn E. Synthesis of Deoxysugars through Manganese-promoted Redox Isomerization |
| title | Synthesis of Deoxysugars through Manganese-promoted Redox Isomerization |
| title_full | Synthesis of Deoxysugars through Manganese-promoted Redox Isomerization |
| title_fullStr | Synthesis of Deoxysugars through Manganese-promoted Redox Isomerization |
| title_full_unstemmed | Synthesis of Deoxysugars through Manganese-promoted Redox Isomerization |
| title_short | Synthesis of Deoxysugars through Manganese-promoted Redox Isomerization |
| title_sort | synthesis of deoxysugars through manganese promoted redox isomerization |
| url | https://hdl.handle.net/1721.1/139107 |
| work_keys_str_mv | AT suhcarolyne synthesisofdeoxysugarsthroughmanganesepromotedredoxisomerization |