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- W2326829585 abstract "A powerful method for the synthesis of 2-oxazolines from silyl-protected β-hydroxyamides is reported. Using diethylaminosulfur trifluoride (DAST) or its tetrafluoroborate salt (XtalFluor-E), silyl-protected β-amidoalcohols can be in situ deprotected and dehydrated to give 2-oxazolines in good yields. The utility of this approach was demonstrated by preparing the first reported oligomer of [2,4′]-coupled 2-oxazoline units. By tuning the stability of the silyl protecting groups (ex. IPDMS < TES < TBS, etc.), the deprotection rate can be optimized so that all reaction intermediates remain soluble, allowing cyclodehydration to occur at all potential sites of ring closure. N-Terminal Ser residues containing an Fmoc carbamate are converted into 2-(9′-fluorenylmethyloxy)-2-oxazoline in high yield, thereby providing a new pathway for the synthesis of peptides capped with an N-terminal 2-alkoxy-2-oxazoline or 2-oxazolidinone unit." @default.
- W2326829585 created "2016-06-24" @default.
- W2326829585 creator A5006008861 @default.
- W2326829585 creator A5006573975 @default.
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- W2326829585 date "2014-12-18" @default.
- W2326829585 modified "2023-10-10" @default.
- W2326829585 title "Synthesis of 2-Oxazolines by <i>in Situ</i> Desilylation and Cyclodehydration of β-Hydroxyamides" @default.
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- W2326829585 doi "https://doi.org/10.1021/jo5016695" @default.
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