2026-09-20T15:10:51Zhttps://dspace.mit.edu/server/oai/requestoai:dspace.mit.edu:1721.1/1391072022-01-15T03:56:28Zcom_1721.1_7582com_1721.1_7581col_1721.1_131023
Wendlandt, Alison
Suh, Carolyn E.
Massachusetts Institute of Technology. Department of Chemistry
2022-01-14T14:50:20Z
2022-01-14T14:50:20Z
2021-06
2021-06-16T17:34:10.697Z
https://hdl.handle.net/1721.1/139107
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.
Massachusetts Institute of Technology
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http://rightsstatements.org/page/InC-EDU/1.0/
Synthesis of Deoxysugars through Manganese-promoted Redox Isomerization
Thesis
application/pdf
Master
Master of Science in Chemistry
Publication
unknown
unknown
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<Abstract>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.</Abstract>
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