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- W3157779072 endingPage "153109" @default.
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- W3157779072 abstract "Inspired by reports of water sculpted Tn antigen (α-GalNAc-O-Ser/Thr) epitopes and our interest in producing metabolically more stable C-linked analogs of Tn, we explored the utility of C2 functionality on α-Gal-C-alkenes to deliver hydroxyl to the pendant alkenyl chain. Toward this end, a cyclic carbonate approach gave rise to a single C-linked α-Gal-1′(S)-hydroxyethane in 3 steps, and use of a 2-(hydroxyimino)galactoside cyclization transferred an oxygen to a pendant cis-substituted C-linked alkene affording the R-configuration at the newly formed stereocenter (7:1 dr). Reduction and acetylation of the resultant isoxazoline demonstrated this approach as a viable route to C-linked α-GalNAc-1′-hydroxyalkanes." @default.
- W3157779072 created "2021-05-10" @default.
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- W3157779072 creator A5060422159 @default.
- W3157779072 date "2021-06-01" @default.
- W3157779072 modified "2023-10-14" @default.
- W3157779072 title "Synthesis of C-linked α-Gal and α-GalNAc-1′-hydroxyalkanes by way of C2 functionality transfer" @default.
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- W3157779072 doi "https://doi.org/10.1016/j.tetlet.2021.153109" @default.
- W3157779072 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/8356801" @default.
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- W3157779072 hasPublicationYear "2021" @default.
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