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- W2034889166 abstract "A one-pot C2-amidoglycosylation reaction for the synthesis of 2-N-acyl-2-deoxy-beta-pyranosides from glycals is described. Glycal donors activated by the reagent combination of thianthrene-5-oxide (11) and Tf2O, followed by treatment with an amide nucleophile and a glycosyl acceptor, lead to the formation of various C2-amidoglycoconjugates. Both the C2-nitrogen transfer and the glycosidic bond formation proceed stereoselectively, allowing for the introduction of both natural and nonnatural amide functionalities at C2 with concomitant anomeric bond formation in a one-pot procedure. Tracking of the reaction by low-temperature NMR spectroscopy employing 15N- and 18O-isotope labels suggests a mechanism involving the formation of the C2-sulfonium glycosyl imidate 39 as well as oxazoline 37 as key intermediates in this novel oxidative glycosylation process." @default.
- W2034889166 created "2016-06-24" @default.
- W2034889166 creator A5035282947 @default.
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- W2034889166 date "2002-07-27" @default.
- W2034889166 modified "2023-10-09" @default.
- W2034889166 title "<i>C2</i>-Amidoglycosylation. Scope and Mechanism of Nitrogen Transfer" @default.
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- W2034889166 doi "https://doi.org/10.1021/ja026281n" @default.
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